Chemfiles 9.3 Cover.Indd 1 6/18/2009 7:49:52 AM Vol

Vol. 9, No. 3

Chiral Building Blocks

Features include: A–Z Product Listings Heterocyclic Building Blocks Organic Building Blocks (S)-(–)-Glycidol: chiral epoxide building block used in synthesis of many pharmaceuticals and natural products

70978 ChemFiles 9.3 cover.indd 1 6/18/2009 7:49:52 AM Vol. 9 No. 3 Introduction Asymmetric synthesis remains a challenge to synthetic chemists as Aldrich Chemical Co., Inc. the demand for enantiomerically pure compounds continues to Sigma-Aldrich Corporation increase. Whether the building blocks are used in the development 6000 N. Teutonia Ave. of new and exciting chiral auxiliaries, ligands, or for obtaining Milwaukee, WI 53209, USA advanced and enantiomerically enriched druglike molecules, research scientists continually need access to a vast array of novel chiral building blocks and architectures to achieve success. To Place Orders In this edition of ChemFiles, we have endeavored to provide a comprehensive listing of over 1000 chiral building blocks. Within Telephone 800-325-3010 (USA) each section of this issue, products are listed by increasing FAX 800-325-5052 (USA) carbon content. Introduction Mark Redlich Sigma-Aldrich is lists over 5000 chiral products for the successful Product Manager Customer & Technical Services construction of complex asymmetric architectures—for a complete listing of products related to chiral chemistry and asymmetric synthesis, please visit us at Customer Inquiries 800-325-3010 sigma-aldrich.com/chiral. If you are unable to find a product for Technical Service 800-231-8327 your research, “Please Bother Us” at [email protected] or contact your local SAFC® 800-244-1173 Sigma-Aldrich office. Custom Synthesis 800-244-1173 If you are viewing the electronic version, simply select a category to jump to that Flavors & Fragrances 800-227-4563 section or activate your Adobe® Bookmarks. You may also search by name, product International 414-438-3850 ® number, molecular formula, or CAS registry number by using the “find” feature in Adobe 24-Hour Emergency 414-438-3850 ® ® (Ctrl+F in Windows or Command+F in a MacIntosh environment). Web Site sigma-aldrich.com Email [email protected] Table of Contents Heterocyclic Building Blocks ...... 3 Amines ...... 30 Subscriptions Furans ...... 3 Amino Alcohols ...... 34 To request your FREE subscription to ChemFiles, Indoles/Indolines/Indolizidines ...... 5 Aziridines ...... 39 please contact us by: Isoquinolines ...... 6 Carboxylic Acids ...... 39 Phone: 800-325-3010 (USA) Morpholines ...... 6 Cyanides/Nitriles ...... 48 Mail: Attn: Marketing Communications Oxazoles/Oxazolines ...... 7 Epoxides ...... 48 Aldrich Chemical Co., Inc. Piperazines ...... 7 Esters ...... 52 Sigma-Aldrich Corporation P.O. Box 355 Piperidines ...... 8 Hydrocarbons ...... 57 Milwaukee, WI 53201-9358 Pyrans ...... 10 Isocyanates/Isocyanides ...... 58 Email: [email protected] Pyridines ...... 10 Ketones ...... 59 Pyrrolidines ...... 11 Lactams/Lactones ...... 62 Quinuclidines ...... 16 Polyamines ...... 64 International customers, please contact your local Sigma-Aldrich ofﬁ ce. For worldwide contact Thiophenes ...... 16 Polyols ...... 65 information, please see back cover. Others ...... 17 Protected Alcohols/Amines ...... 68 ChemFiles are also available in PDF format on the Sulfonamides/Sulfinamides ...... 69 Organic Building Blocks ...... 21 Internet at sigma-aldrich.com/chemﬁ les. Sulfonates/Sulfinates ...... 70 Acid Halides ...... 21 Others ...... 70 Alcohols ...... 21 Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that Aldehydes ...... 28 Risk and Safety Information ...... 74 its products conform to the information contained Amides ...... 29 in this and other Sigma-Aldrich publications. Purchaser must determine the suitability of the product for its particular use. See reverse side of invoice or packing slip for additional terms and About Our Cover conditions of sale. The image on our cover represents the three dimensional structure of (S)-(–)-Glycidol. This chiral epoxide is a common building block used in synthesis of many All prices are subject to change without notice. pharmaceuticals and natural products. ChemFiles (ISSN 1933–9658) is a publication of Aldrich Chemical Co., Inc. Aldrich is a member of the Sigma-Aldrich Group. © 2009 Sigma-Aldrich Co.

70978 ChemFiles 9.3 cover.indd 2 6/18/2009 7:49:58 AM Heterocyclic Building Blocks

Furans Blocks Building Heterocyclic (S)-(+)-3‑Hydroxytetrahydrofuran, (S)-(+)-5‑Oxo-2‑tetrahydrofuran- (R)-Tetrahydrofurfuryl alcohol, 99% carboxylic acid, 98% ≥98.0% (GC, sum of enantiomers)

‑ ‑ ‑ ‑ ‑ ‑ [86087 23 2] OH [21461 84 7] [22415 59 4] OH OH C4H8O2 C5H6O4 O O C5H10O2 O FW 88.11 O FW 130.10 O FW 102.13

296686 301469 89095

(R)-(−)-3‑Hydroxytetrahydrofuran, (R)-Tetrahydrofuran-2‑carbonitrile, (S)-(+)-Tetrahydrofurfurylamine, 98% ≥98.0% (GC, sum of enantiomers) 97% ‑ ‑ [86087‑24‑3] [164472‑78‑0] [7175 81 7] OH NH2 C5H7NO C5H11NO O C4H8O2 O CN FW 88.11 O FW 97.12 FW 101.15 67948 412945 309753 (R)-(−)-Tetrahydrofurfurylamine, (R)-(+)-Tetrahydro-3‑furylamine (S)-(+)-Dihydro-5-(hydroxymethyl)- 99% p-toluenesulfonate salt, ≥99.0% (T) 2(3H)-furanone, 95% ‑ ‑ ‑ ‑ [32780‑06‑6] [7202 43 9] [111769 27 8] – NH2 + SO3 HO C H NO NH3 C5H8O3 O O 5 11 O C4H9NO · C7H8O3S FW 116.12 FW 101.15 FW 259.32 O 348902 412937 CH3 − ‑ ≥ 09440 (R)-(−)-Dihydro-5-(hydroxymethyl)- (S)-( )-1-(2 Furyl)ethanol, 99.0% 2(3H)-furanone, 97% (GC, sum of enantiomers) (R)-(+)-5‑Hydroxymethyl-2(5H)- [52813‑63‑5] [85828‑09‑7] ≥ HO CH furanone, 97.0% (HPLC, sum of O C H O 3 C5H8O3 O 6 8 2 O enantiomers) FW 116.12 FW 112.13 OH [112837‑17‑9] 343544 48188 HO C5H6O3 O O FW 114.10 (R)-(+)-Tetrahydro-2‑furoic acid, Benzyl (S)-(−)-tetrahydro-5‑oxo- 55673 99% 3‑furanylcarbamate, 97%

‑ ‑ [87219‑29‑2] − ‑ [87392 05 0] H (S)-( )-5 Hydroxymethyl-2(5H)- OH N C5H8O3 O C12H13NO4 Cbz furanone, 98% O FW 116.12 FW 235.24 O O ‑ ‑ [78508 96 0] 479292 419249 HO C5H6O3 O O FW 114.10 − ‑ (S)-( )-Tetrahydro-2 furoic acid, [3aR(3aα,4α,5β,6aα)]-(−)-5- 346861 98% (Benzoyloxy)hexahydro-2‑oxo-2H- ‑ ‑ cyclopenta[b]furan-4‑carboxal- (R)-(−)-5‑Oxo-2‑tetrahydrofuran- [87392 07 2] C H O OH dehyde, 95% carboxylic acid, 98% 5 8 3 O FW 116.12 O [39746‑01‑5] O [53558‑93‑3] O 527890 C15H14O5 OH O O C5H6O4 O O FW 274.27 O FW 130.10 H (S)-(−)-Tetrahydrofuran-2‑carbox- O 310476 amide, 97% 480517

C5H9NO2 NH2 FW 115.13 O O

573310

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 3 (3aR)-(+)-Sclareolide, 97% (+)-Noe-lactol® dimer, ≥99% (−)-Noe-lactol® dimer, ≥99%

[564‑20‑5] [87248‑50‑8] [108031‑79‑4] O CH3 H C H C CH H3C CH3 H3C 3 CH3 3 3 C16H26O2 H C C24H38O3 C24H38O3 CH3 3 O H3C FW 250.38 CH FW 374.56 FW 374.56 3 O O H C O O CH3 3 O O H3C CH3

358002 254827 263907

(−)-Ambroxide, 99%

[6790‑58‑5] H3C O C16H28O FW 236.39 CH3 H3C H CH3

379220 Heterocyclic Building Blocks

Rare Chemical Library The Sigma-Aldrich® Rare Chemical Library consists of over 140,000 unique chemical compounds, including: • Private and academic collections released upon the researcher’s retirement • One-time synthetic series from remote and obscure sources FREE! • Products no longer available from the Sigma-Aldrich catalogs Request the Rare Chemical Library • Plus synthetic analogs and precursors compound list on USB ﬂ ash drive. • Available in standard sizes between 1mg and 1g Visit sigma-aldrich.com/rcl to ﬁ nd out more about this DiscoveryCPR unique service.

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sigma-aldrich.com

4 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Indoles/Indolines/Indolizidines (1S,6S,7R,8R,8aR)-1,6,7,8‑Tetra- (3R)-(−)-3-(1‑Methyl-1H-indol-3‑yl) (3S)-(+)-3-(1‑Methylindol-3‑yl)- hydroxyindolizidine, 98% butyraldehyde, 98% 3‑phenylpropionaldehyde, 97%

[79831‑76‑8] Blocks Building Heterocyclic OH C13H15NO CH3 O C18H17NO H OH C8H15NO4 HO FW 201.26 FW 263.33 H O FW 189.21 N HO N H CH3 532673 N 591882 CH3 (S)-(+)-2‑Indolinemethanol, 97% 591017 (3S)-(+)-3-(1‑Methyl-1H-indol-3‑yl)- ‑ ‑ ‑ [27640 33 1] OH 1 butanol, 98% (3R)-(−)-3-(methyl-1H-indol-3‑yl)- C9H11NO N 3‑phenylpropionic acid, 97% H FW 149.19 C13H17NO CH3 FW 203.28 523720 OH C18H17NO2 FW 279.33 N O CH3 (S)-(+)-α-Hydroxy-1,3‑dioxo-2‑iso- OH

indolinebutyric acid, 98% 592005 N

CH3 ‑ ‑ [48172 10 7] O − ‑ O Methyl (3R)-( )-3-(1 methylindol- 591734 C12H11NO5 N ‑ FW 249.22 OH 3 yl)butanoate, 98% OH O Methyl (3S)-(+)-3-(methyl-1H-indol- C H NO 14 17 2 CH3 O ‑ ‑ 409650 FW 231.29 3 yl)-3 phenylpropionate, 98% OCH3

N C19H19NO2 (3S)-(−)-3-(1‑Methyl-1H-indol-3‑yl) CH 3 FW 293.36 butanenitrile, 98% O 591564 OCH3

C13H14N2 CH3 N FW 198.26 CN (3S)-(+)-3-(1‑Methylindol-3‑yl)- CH3 ‑ N 3 phenylpropionitrile, 98% 591653 CH3 C H N 18 16 2 − ‑ 591785 FW 260.33 ( )-7 Octylindolactam V, ~90% CN [109346‑66‑9] ‑ ‑ CH3 (3S)-(+)-3-(1 Methyl-1H-indol-3 yl)- H3C N C25H39N3O2 H 1‑butyraldehyde, 97% N CH3 FW 413.60 H3C N OH O [406920‑65‑8] CH3 O 591246 C H NO N 13 15 H H FW 201.26 CH3 N CH3 O1631

591343

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 5 Isoquinolines (S)-1,2,3,4‑Tetrahydro-3‑isoquino- (S)-(−)-N-tert-Butyl-1,2,3,4‑tetra- (R)-(+)-1-(4‑Methoxybenzyl)- linecarboxylic acid, ≥97.0% (T) hydro-3‑isoquinolinecarboxamide, 1,2,3,4,5,6,7,8‑octahydroisoquino- 98% line, 97% ‑ ‑ [74163 81 8] O C H NO ‑ ‑ ‑ ‑ 10 11 2 OH [149182 72 9] O [30356 08 2] CH3 FW 177.20 NH C14H20N2O C17H23NO N CH3 NH H FW 232.32 NH CH3 FW 257.37 87437

493740 OCH3 (S)-(−)-1,2,3,4‑Tetrahydro-3‑isoquinolinemethanol, 98% [3S-(3α,4aβ,8aβ)]-N-(tert-Butyl) 539007 decahydro-3‑isoquinolinecarbox- [18881‑17‑9] (S)-(+)-2-(Benzyloxycarbonyl)- OH amide, 98% C10H13NO NH 1,2,3,4‑tetrahydro-3‑isoquinoline- FW 163.22 ‑ ‑ [136465 81 1] O carboxylic acid, 97% H CH3 494186 C14H26N2O N CH3 ‑ ‑ Heterocyclic Building Blocks H [79261 58 8] FW 238.37 NH CH3 O H C H NO (S)-(−)-6,7‑Dimethoxy-1,2,3,4‑tetra- 18 17 4 OH FW 311.33 N hydroisoquinoline-3‑carboxylic 468916 Cbz

acid hydrochloride, 97% 465054 Benzyl (S)-(−)-1,2,3,4‑tetrahydro- [82586‑62‑7] O 3‑isoquinolinecarboxylate p-tolue- − ‑ α α C12H15NO4 · HCl H3CO (S)-( )-1,2,3,4 Tetrahydro- , -di- OH nesulfonic acid salt, 97% ‑ FW 273.71 NH • HCl phenyl-3 isoquinolinemethanol, H CO 3 97% O O 543527 S OH O ‑ ‑ • O [140408 82 8] NH H3C C22H21NO OH [77497‑97‑3] FW 315.41 NH C17H17NO2 ·C7H8O3S FW 439.52 496057 465062

Morpholines (R)-4‑Boc-3‑morpholineacetic acid, (2S,3R)-(+)-N-Boc-6‑oxo- (2S,3R)-(+)-N-Z-6‑oxo-2,3‑diphenyl- ≥97.5% (HPLC) 2,3‑diphenylmorpholine, 99% morpholine, 99%

[761460‑03‑1] [112741‑50‑1] [105228‑46‑4] Boc Boc Cbz C11H19NO5 N OH C21H23NO4 N C24H21NO4 N FW 245.27 O FW 353.41 FW 387.43 O O O O O 669830 331813 331856 (S)-4‑Boc-3‑morpholineacetic acid, ≥97.5% (HPLC) (2R,3S)-(−)-N-Boc-6‑oxo- (2R,3S)-(−)-N-Z-6‑oxo-2,3‑diphenyl- 2,3‑diphenylmorpholine, 99% morpholine, 98% ‑ ‑ [839710 38 2] Boc C11H19NO5 N OH [112741‑49‑8] [100516‑54‑9] Boc Cbz FW 245.27 O O C21H23NO4 N C24H21NO4 N FW 353.41 FW 387.43 669954 O O O O

(S)-(−)-N-Boc-5‑benzyl-2‑oxo- 331848 331872 morpholine, 99%

‑ ‑ [130317 10 1] Boc C16H21NO4 N FW 291.34 O O

479926

6 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Oxazoles/Oxazolines Methyl (S)-(+)-4,5‑dihydro-2‑phe- Methyl (4S,5S)-dihydro-5‑methyl- Ethyl (2S)-(+)-2-[4-(6‑chloro- nyl-4‑oxazolecarboxylate, 96% 2‑phenyl-4‑oxazolecarboxylate, benzoxazol-2‑yloxy)phenoxy] 98% propanoate, 95% [78715‑83‑0] Blocks Building Heterocyclic O

C11H11NO3 H3C [82659‑84‑5] O N O N O FW 205.21 C12H13NO3 CH O H3CO N Cl O 3 FW 219.24 O CH3 H3C O O 516058 O [113776‑20‑8] − ‑ ‑ 292176 (4S,5S)-( )-2 Methyl-5 phenyl- C18H16ClNO5 2‑oxazoline-4‑methanol, 98% FW 361.78 (4S,5S)-(−)-4,5‑Dihydro-4‑methoxy- 542776 [53732‑41‑5] ‑ ‑ HO N methyl-2 methyl-5 phenyloxazole, C11H13NO2 O CH 97% FW 191.23 3 [52075‑14‑6] H3CO N 187666 C12H15NO2 O CH3 FW 205.25

187658

Piperazines (R)-3‑Methyl-2‑ketopiperazine, (S)-(+)-2‑Methylpiperazine, 99% (S)-3-tert-Butyl-2,5‑piperazine- ≥99.0% (GC) dione, ≥99.0% (CHN) ‑ ‑ [74879 18 8] H N C5H12N2 [65050‑07‑9] C5H10N2O H H N CH3 N O FW 114.15 FW 100.16 N CH3 C8H14N2O2 H N O FW 170.21 O N t-Bu H 397172 H 51989 20550 (R)-(−)-3‑Isopropyl-2,5‑piperazine- (S)-3‑Methyl-2‑ketopiperazine, dione, 97% (R)-1‑Boc-3‑methylpiperazine, 97% ≥99.0% (GC) [143673‑66‑9] ‑ ‑ H [163765 44 4] H N O ‑ ‑ C H N O N CH3 [78551 38 9] H 7 12 2 2 C10H20N2O2 N CH3 CH3 C5H10N2O FW 156.18 O N FW 200.28 N H CH3 Boc FW 114.15 N O H 448362 674761 73525 (S)-3‑Isopropyl-2,5‑piperazine- (S)-1‑Boc-3‑methylpiperazine, ‑ (R)-2 Piperazinecarboxylic acid dione, ≥99.0% (HPLC, sum of ≥98.0% (GC) ≥ dihydrochloride, 98.0% (T) enantiomers) ‑ ‑ [147081 29 6] H [126330‑90‑3] N CH3 H • 2 HCl ‑ ‑ C10H20N2O2 N [16944 60 8] H C5H10N2O2 · 2HCl O N FW 200.28 N OH C7H12N2O2 FW 203.07 N Boc H FW 156.18 O N CH3 O H CH3 63207 67176 59732 (R)-(−)-2‑Methylpiperazine, 97%

‑ ‑ [75336 86 6] H N C5H12N2

FW 100.16 N CH3 H

397164

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 7 (2S-cis)-(−)-5‑Benzyl-3,6‑dioxo- (R)-(−)-α-[[(4‑Ethyl-2,3‑dioxo-1‑ (R)-(−)-α-[[(4‑Ethyl-2,3‑dioxo-1‑ 2‑piperazineacetic acid, 97% piperazinyl)carbonyl]amino]ben- piperazinyl)carbonyl]amino]- zeneacetic acid, 97% 4‑hydroxybenzeneacetic acid, 97% ‑ ‑ [5262 10 2] H N O O ‑ ‑ ‑ ‑ C13H14N2O4 [63422 71 9] [62893 24 7] HO O O FW 262.26 O N OH C15H17N3O5 C15H17N3O6 H OH FW 319.31 FW 335.31 OH HN O HN O 421650 N O N O

N O N O CH 3 CH3

472891 472905

Piperidines (R)-(+)-3‑Hydroxypiperidine hydro- (R)-(–)-3‑Piperidinecarboxylic acid, (R)-1‑Boc-3‑hydroxypiperidine,

Heterocyclic Building Blocks chloride, 98% 97% 95% ‑ ‑ ‑ ‑ ‑ ‑ [198976 43 1] OH [25137 00 2] O [143900 43 0] OH C H NO · HCl C H NO C H NO 5 11 • HCl 6 11 2 OH 10 19 3 N N FW 137.61 H FW 129.16 FW 201.26 N Boc H 410462 687278 656356 (S)-3‑Hydroxypiperidine hydro- ‑ (S)-1‑Boc-3‑hydroxypiperidine, chloride, ≥98.0% (AT) (S)-(+)-3 Piperidinecarboxylic acid, 97% 97% [475058‑41‑4] OH [143900‑44‑1] [59045‑82‑8] OH C5H11NO · HCl O HCl C10H19NO3 N C6H11NO2 FW 137.61 H OH FW 201.26 N FW 129.16 Boc N 30169 H 687367 656364 (R)-(−)-3‑Aminopiperidine dihydro- (R)-(−)-3‑Amino-1‑Boc-piperidine, chloride, 97% ‑ (S)-(+)-2 Methylpiperidine, 97% ≥98.0% (TLC) [334618‑23‑4] NH2 [3197‑42‑0] [188111‑79‑7] C5H12N2 · 2HCl • 2HCl NH2 C6H13N N N CH3 C10H20N2O2 FW 173.08 H FW 99.17 H FW 200.28 N Boc 666297 522902 07858 (S)-(+)-3‑Aminopiperidine dihydro- (R)-2‑Piperidineethanol hydro- ‑ ‑ chloride, 96% chloride, ≥98.0% (GC) (S)-(+)-3 Amino-1 Boc-piperidine, ≥98.0% (TLC) ‑ ‑ [334618 07 4] NH [787622‑24‑6] 2 • HCl ‑ ‑ C5H12N2 · 2HCl C H NO · HCl [625471 18 3] NH • 2HCl 7 15 2 N N OH FW 173.08 H FW 165.66 H C10H20N2O2 FW 200.28 N 674109 670057 Boc 19929 (S)-6‑Oxo-2‑piperidinecarboxylic (S)-2‑Piperidineethanol hydro- acid, ≥95.0% (HPLC) chloride, ≥98.0% (GC) (S)-3-(Boc-amino)piperidine, ≥ ‑ ‑ [786684‑21‑7] 98.0% (TLC) [34622 39 4] • HCl C6H9NO3 OH C7H15NO · HCl ‑ ‑ O N N OH [216854 23 8] H FW 143.14 H FW 165.66 H N O C10H20N2O2 Boc 670170 FW 200.28 N 36323 H

08601

8 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-1‑Boc-4‑oxopiperidine- (R)-(−)-1‑Benzyl-3‑hydroxypiper- (R)-(+)-1‑Cbz-2‑piperidinecarboxy- 2‑carboxylic acid, 95% idine, 97% lic acid, 97%

[91599‑81‑4] [28697‑09‑8] C11H17NO5 O OH FW 243.26 C12H17NO C14H17NO4 OH N N OH FW 191.27 FW 263.29 Blocks Building Heterocyclic N Cbz O Boc O 516376 676322 455172 D-(+)-Vesamicol hydrochloride (R)-1-Boc-4-oxopiperidine-2- 8 ‑ ‑ ‑ ‑ carboxylic acid, 97% (S)-1 Boc-2 piperidineacetic acid, [112709 60 1] Ph ≥99.0% (HPLC) C17H25NO · HCl • HCl C11H17NO5 O FW 295.85 ‑ ‑ N FW 243.26 [159898 10 9] OH O OH C12H21NO4 N N OH Boc O FW 243.30 Boc V104 701130 669725 (−)-Lobeline hydrochloride, 98% (S)-1‑Boc-piperidine-3‑carboxylic (R)-1‑Boc-2‑piperidineacetic acid, acid, 97% ≥ [134‑63‑4] 99.0% (HPLC) O OH • HCl C22H27NO2 · HCl ‑ ‑ N [88495 54 9] O [351410‑32‑7] FW 373.92 C H NO O CH3 11 19 4 OH C12H21NO4 FW 229.27 N OH N FW 243.30 Boc 141879 Boc 669628 681229 (R)-(−)-2‑Piperidino-1,1,2‑triphenylethanol, 97% Ethyl (S)-N-Boc-piperidine-3- 8 (S)-(+)-N-(Boc)-2‑methylpiperidine, carboxylate, 95% [213995‑12‑1] 98% C25H27NO [191599‑51‑6] N O FW 357.49 [183903‑99‑3] C13H23NO4 O CH3 HO C11H21NO2 FW 257.33 N N CH3 FW 199.29 Boc Boc 647462 522880 696404 ‑ ‑ (S)-1‑Benzyl-3‑hydroxypiperidine, (S)-(−)-1‑Cbz-2‑piperidinecarboxylic (S)-(+)-2 Piperidino-1,1,2 triphenyl- ≥97.0% (GC) acid, 97% ethanol, 97% [869495‑24‑9] [91599‑79‑0] [28697‑11‑2] OH C H NO C H NO C14H17NO4 OH 25 27 12 17 N N N FW 357.49 FW 191.27 FW 263.29 Cbz O HO 499587

28964 647470

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 9 Pyrans (S)-6‑Chloromethyl-5,6‑dihydro- (R)-(+)-6‑Hydroxy-2,5,7,8‑tetra- (+)-Catechin hydrate, ≥96.0% pyran-2‑one, ≥98.0% (GC) methylchroman-2‑carboxylic acid, (HPLC, sum of enantiomers) 98% ‑ ‑ ‑ ‑ [135999 61 0] [225937 10 0] OH OH C6H7ClO2 Cl [53101‑49‑8] C15H14O6 ·xH2O O O CH • xH2O FW 146.57 3 FW 290.27 (Anh) C14H18O4 HO O HO O 16749 FW 250.29 OH H C O OH 3 CH3 OH CH3 (3aS,4R,6S,7aS)-Tetrahydro- 22110 4‑hydroxymethyl-6‑methoxy-4H- 391913 furo[3,2-c]pyran-2(3H)-one, ≥98% ‑ α (S)-(−)-6‑Hydroxy-2,5,7,8‑tetra- 2,3,4,6 Tetra-O-benzyl- -D-gluco- ‑ ‑ ‑ pyranosyl trichloroacetimidate [62158 33 2] OH methylchroman-2 carboxylic acid, C9H14O5 H 98% [74808‑09‑6] O RO FW 202.20 O C36H36Cl3NO6 H CO O ‑ ‑ O 3 [53174 06 4] R = CH H CH3 OR NH 2

Heterocyclic Building Blocks FW 685.03 C H O HO O 14 18 4 O CCl3 T8175 OR FW 250.29 OH OR H C O 3 CH3 CH3 (3aS,4R,6R,7aS)-Tetrahydro- 524352 4‑hydroxymethyl-6‑methoxy-4H- 391921 furo[3,2-c]pyran-2(3H)-one, ≥98%

‑ ‑ [62210 98 4] OH C9H14O5 H O FW 202.20 O H CO O 3 H

T8050

Pyridines (R)-α-Methyl-2‑pyridinemethanol, (S)-(−)-α-Methyl-4‑pyridinemeth- (3R,5S,8aR)-(−)-Hexahydro-3‑phe- ≥98.0% (GC) anol, 99% nyl-5H-oxazolo[3,2-a]pyridine- 5‑carbonitrile, 97% [27911‑63‑3] [54656‑96‑1] H3C OH C7H9NO CH C7H9NO [88056‑92‑2] N 3 FW 123.15 OH FW 123.15 C14H16N2O CN N FW 228.29 N 41304 448540 O H (S)-α-Methyl-2‑pyridinemethanol (S)-N-Boc-1,2,3,6‑tetrahydro-2‑pyri- 642118 [59042‑90‑9] dinecarboxylic acid, ≥98.0% (HPLC) [2S-(2α,3β,8aβ)]-(+)-Hexahydro-3- C7H9NO CH N 3 [417726‑36‑4] (hydroxymethyl)-8a-methyl-2‑phe- FW 123.15 OH C11H17NO4 OH N nyl-5H-oxazolo[3,2-a]pyridin- FW 227.26 06368 Boc O 5‑one, 98% 670286 ‑ ‑ (R)-(+)-α-Methyl-4‑pyridinemeth- [116950 01 7] O C H NO anol, 99% 15 19 3 N OH (3S,5R,8aS)-(+)-Hexahydro-3‑phe- FW 261.32 O [27854‑88‑2] nyl-5H-oxazolo[3,2-a]pyridine- CH3 H3C OH C7H9NO 5‑carbonitrile, 97% 388114 FW 123.15 N [106565‑71‑3] C H N O CN 448532 14 16 2 FW 228.29 N O H

642002

10 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Pyrrolidines (R)-(+)-4‑Hydroxy-2‑pyrrolidinone, (S)-(−)-3‑Aminopyrrolidine, 98% (S)-(+)-2‑Pyrrolidinemethanol, 97% 97% [128345‑57‑3] [23356‑96‑9] NH2 ‑ ‑ OH Blocks Building Heterocyclic [22677 21 0] HO C4H10N2 C5H11NO N H N C4H7NO2 FW 86.14 H FW 101.15 O FW 101.10 N 186511 H 540803 479160 (R)-(−)-2‑Pyrrolidinemethanol, 99% (R)-(+)-3‑Aminopyrrolidine, 98% (S)-(−)-4‑Hydroxy-2‑pyrrolidinone, [68832‑13‑3] [116183‑82‑5] OH 97% NH2 C5H11NO N C H N H 4 10 2 FW 101.15 ‑ ‑ FW 86.14 N [68108 18 9] HO H 281697 C4H7NO2 540781 FW 101.10 N O H (R)-(−)-1‑Methyl-3‑pyrrolidinol

479179 (R)-(–)-2-(Trifluoromethyl) ‑ ‑ [104641 60 3] OH pyrrolidine, 97% C H NO ‑ 5 11 (S)-(+)-3 Fluoropyrrolidine hydro- FW 101.15 N [119618‑29‑0] chloride, 97% CH3 C5H8F3N N CF3 ‑ ‑ FW 139.12 H 647241 [136725 53 6] F C4H8FN · HCl 680087 • HCl ‑ ‑ FW 125.57 N (S)-(+)-1 Methyl-3 pyrrolidinol, H (S)-(+)-2-(Trifluoromethyl) 95% 637513 pyrrolidine, 97% ‑ ‑ [104641 59 0] OH C H NO (R)-(−)-3‑Fluoropyrrolidine hydro- [119580‑41‑5] 5 11 FW 101.15 N C5H8F3N CF3 chloride, 97% N CH3 FW 139.12 H ‑ ‑ [136725 55 8] F 665614 573337 C4H9ClFN • HCl FW 125.57 N H (R)-(−)-5-(Hydroxymethyl)- (S)-(+)-2-(Aminomethyl)pyrrolidin- e, 97% 637505 2‑pyrrolidinone, 99% ‑ ‑ [66673‑40‑3] [69500 64 7] ‑ ≥ NH2 (S)-3 Pyrrolidinol, 97.0% HO O C5H12N2 N C5H9NO2 N H (GC, sum of enantiomers) FW 115.13 H FW 100.16 422886 [100243‑39‑8] 366358 OH C H NO 4 9 cis-3‑Azabicyclo[3.1.0]hexane- FW 87.12 N (S)-5-(Hydroxymethyl)- H ‑ 2‑pyrrolidinone, 97% 2 carboxylic acid, 98% 56437 [22255‑16‑9] [17342‑08‑4] H H HO C6H9NO2 O C5H9NO2 N O (R)-3‑Pyrrolidinol, 98% H FW 127.14 N FW 115.13 H OH [2799‑21‑5] 366366 OH 391190 C4H9NO FW 87.12 N (R)-(−)-2‑Methylpyrrolidine H Methyl (S)-(+)-2‑pyrrolidone- ‑ ‑ 5‑carboxylate, 97% 382981 [41720 98 3] C H N CH3 5 11 N [4931‑66‑2] FW 85.15 H − ‑ H3CO (R)-( )-3 Pyrrolidinol hydro- C6H9NO3 N O chloride, 98% 679097 FW 143.14 O H ‑ ‑ ‑ 463396 [104706 47 0] OH (S)-(+)-2 Methylpyrrolidine, 90% C4H9NO · HCl • HCl ‑ ‑ FW 123.58 N [59335 84 1] H C5H11N N CH3 H 430722 FW 85.15 649147

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 11 N-[(2S)-2‑Pyrrolidinylmethyl]-tri- (S)-(−)-2-(Methoxymethyl)- (S)-(+)-N-Boc-3‑pyrrolidinol, 97% fluoromethanesulfonamide, 1‑pyrrolidinecarboxaldehyde, 98% [101469‑92‑5] ≥98.5% (T) OH [63126‑45‑4] C9H17NO3 ‑ ‑ C H NO OCH3 FW 187.24 N [782495 18 5] O 7 13 2 N H Boc C6H11F3N2O2S N S CF3 FW 143.18 N H O FW 232.22 H O 634786 277061 689017 (R)-(+)-1‑Boc-3‑aminopyrrolidine, (S)-(−)-2‑Aminomethyl-1‑ethyl- − ‑ 97% (2R,5R)-( )-trans-2,5 Dimethyl- pyrrolidine, 96% ≥ pyrrolidine, 97.0% (GC) ‑ ‑ [147081 49 0] NH [22795‑99‑9] 2 ‑ ‑ NH2 C9H18N2O2 [62617 70 3] C H N 7 16 2 N FW 186.25 N C H N H C CH3 6 13 3 N FW 128.22 Boc FW 99.17 H CH3 644064 41566 647446 − ‑ ‑ (R)-(+)-2-Aminomethyl-1- 8 (S)-( )-1 Boc-3 aminopyrrolidine,

Heterocyclic Building Blocks (R)-(+)-3-(Dimethylamino) pyrrolidine, 95% ethylpyrrolidine, 90% 95% ‑ ‑ [147081‑44‑5] ‑ ‑ [22795 97 7] NH2 [132958 72 6] NH2 H3C C7H16N2 N C9H18N2O2 C6H14N2 N CH3 N FW 128.22 CH FW 186.25 FW 114.19 3 Boc N H 681709 634794 656712 8 (S,S)-2,2′-Bipyrrolidine D-tar- (R)-3-(Boc-amino)pyrrolidine, (S)-(−)-3-(Dimethylamino) trate trihydrate, 99% ≥98.0% (TLC) pyrrolidine, 97% OH O [122536‑77‑0] H • HO H ‑ ‑ OH N [132883 44 4] C9H18N2O2 Boc H3C N N O OH H H C H N N H 6 14 2 CH3 FW 186.25 N • 3H2O H FW 114.19 N H C8H16N2 ·C4H6O6 ·3H2O 56308 FW 344.36 656704 688746 (S)-3-(Boc-amino)pyrrolidine, ≥ ‑ 98.0% (TLC) (R)-(+)-1 Amino-2-(methoxy- (S,S)-(+)-2,5‑Bis(methoxymethyl) methyl)pyrrolidine, 96% ‑ ‑ pyrrolidine, ≥97.0% (GC, sum of [122536 76 9] H N C9H18N2O2 Boc [72748‑99‑3] enantiomers) FW 186.25 N C H N O OCH3 H 6 14 2 N [93621‑94‑4] FW 130.19 NH2 H CO 3 OCH3 52927 C8H17NO2 N 281581 FW 159.23 H ‑ 15022 N-Boc-4,4 difluoro-L-proline, 97% − ‑ (S)-( )-1 Amino-2-(methoxy- ‑ ‑ [203866 15 3] F methyl)pyrrolidine, 95% Butyl (S)-(−)-2‑pyrrolidone- F C10H15F2NO4 5‑carboxylate, 98% OH [59983‑39‑0] FW 251.23 N Boc O OCH3 C6H14N2O N [4931‑68‑4] FW 130.19 NH2 O CH3 687340 C9H15NO3 O N H O 281573 FW 185.22 N-Boc-4‑oxo-L-proline, 97% 440329 (S)-(−)-N-(Trifluoroacetyl) [84348‑37‑8] ‑ − ‑ O pyrrolidine-2 carbonyl chloride (R)-( )-N-Boc-3 pyrrolidinol, 98% C10H15NO5 OH solution FW 229.23 N ‑ ‑ O [109431 87 0] OH Boc [36724‑68‑2] C9H17NO3 681202 Cl N C7H7ClF3NO2 N FW 187.24 Boc FW 229.58 O F3C O 532169 248509

12 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. N-Boc-trans-4‑fluoro-L-proline, (R)-(+)-1‑Benzyl-3‑pyrrolidinol, (S)-(+)-1‑Benzyl-3‑amino- 97% 98% pyrrolidine, 97%

[203866‑14‑2] [101930‑07‑8] [114715‑38‑7] F OH NH2 C10H16FNO4 C11H15NO C11H16N2 OH

FW 233.24 N FW 177.24 N FW 176.26 N Blocks Building Heterocyclic Boc O

687332

366935 536598 N-Boc-cis-4‑fluoro-L-proline, 97% (S)-(−)-1‑Benzyl-3‑pyrrolidinol, − ‑ ‑ [203866‑13‑1] (R)-( )-1 Benzyl-3 amino- F 99% C10H16FNO4 pyrrolidine, 95% OH FW 233.24 N ‑ ‑ O [101385 90 4] ‑ ‑ Boc OH [114715 39 8] NH2 C11H15NO C11H16N2 687324 FW 177.24 N FW 176.26 N (R)-(+)-1‑Boc-2‑pyrrolidinecarbo- nitrile, 97% 366943 536601 C H N O 10 16 2 2 − ‑ ‑ − FW 196.25 N CN (3R,4R)-( )-1 Benzyl-3,4 pyrrolidin- (R)-( )-2-(Anilinomethyl)pyrro- Boc ediol, ≥97.0% (HPLC, sum of enan- lidine, 97% 647233 tiomers) [68295‑45‑4] H ‑ ‑ C H N N [163439 82 5] HO OH 11 16 2 N − ‑ ‑ H (S)-( )-1 Boc-2 pyrrolidinecarbo- C11H15NO2 FW 176.26 nitrile, 97% FW 193.24 N 510505 [228244‑04‑0] C H N O 10 16 2 2 N CN N-Boc-4-oxo-L-proline methyl 8 Boc 37034 FW 196.25 ester, 97% 542091 ‑ ‑ (3S,4S)-(+)-1‑Benzyl-3,4‑pyrrolidin- [102195 80 2] O ≥ C11H17NO5 ‑ ediol, 97.0% (HPLC, sum of enan- OCH3 (R)-2-(Azidomethyl)-1 Boc- FW 243.26 N pyrrolidine, ≥95% (HPLC) tiomers) Boc O [90365‑74‑5] 702498 [259537‑91‑2] HO OH N 3 C11H15NO2 C10H18N4O2 N 8 FW 226.28 Boc FW 193.24 N N-Boc-trans-4-fluoro-L-pro-

670006 line methyl ester, 97% ‑ ‑ [203866 18 6] F 52057 (S)-2-(Azidomethyl)-1‑Boc- C11H18FNO4 OCH3 pyrrolidine, ≥95% (HPLC) FW 247.26 N 1-(p-Tosyl)-(R)-(−)-3‑pyrrolidinol, Boc O ‑ ‑ [168049 26 1] 98% 702412 N3 C10H18N4O2 N Boc [133034‑00‑1] FW 226.28 OH (S)-(−)-1‑Boc-3‑acetamido- C11H15NO3S 669881 FW 241.31 N pyrrolidine, 97% O S O [114636‑37‑2] (S)-N-Boc-2‑methylpyrrolidine, H N CH3 C11H20N2O3 95% O FW 228.29 N CH3 [137496‑71‑0] Boc

C10H19NO2 N CH3 532150 665088 FW 185.26 Boc

687588 (R)-(+)-1‑Boc-3‑acetamido- pyrrolidine, 97% ‑ ‑ [550371 67 0] H N CH3 C11H20N2O3 O FW 228.29 N Boc

665061

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 13 (S,S)-N-Boc-2,5‑dimethyl- (R)-(+)-1‑Benzylpyrrolidine-2‑meth- (1S,2R)-1‑Phenyl-2-(1‑pyrrolidinyl)- pyrrolidine, 95% anol, ≥95.0% (GC) 1‑propanol, 98% ‑ ‑ ‑ ‑ C11H21NO2 [182076 49 9] [56571 91 6] OH FW 199.29 H3C N CH3 C12H17NO N C13H19NO N Boc FW 191.27 FW 205.30 CH3 OH 688525 68416 548979 (S)-1-[(1‑Methyl-2‑pyrrolidinyl) methyl]piperidine, 97% (1′R,3R)-(+)-1-(1′-Phenylethyl)- (S)-(−)-1-(2‑Methoxybenzoyl)-2- 5‑oxo-3‑pyrrolidinecarboxylic acid, (methoxymethyl)pyrrolidine, 99% [84466‑85‑3] 97% C11H22N2 N [102069‑84‑1] N OCH3 FW 182.31 CH ‑ ‑ C14H19NO3 N 3 [99735 43 0] O FW 249.31 C H NO O 446351 13 15 3 OH FW 233.26 OCH O N 3

(R)-(−)-1‑Cbz-3‑pyrrolidinol, 95% H3C 348368 Heterocyclic Building Blocks [100858‑33‑1] OH 534366 (R)-N-Boc-2‑phenylpyrrolidine C12H15NO3 FW 221.25 N [174311‑02‑5] Cbz (S)-(−)-1-(2‑Methoxybenzoyl)- ‑ C15H21NO2 N 654655 2 pyrrolidinemethanol, 99% FW 247.33 Boc

[102069‑83‑0] 685291 (S)-(+)-1‑Cbz-3‑pyrrolidinol, 95% OH C13H17NO3 CH3O N FW 235.28 ‑ ‑ O (S)-(−)-1‑Benzyl-3-(Boc-amino) [100858 32 0] OH C12H15NO3 pyrrolidine, 97% FW 221.25 N 345628 Cbz C16H24N2O2 H N FW 276.37 Boc 654663 ‑ (R)-(+)-1-(2 Methoxybenzoyl)- N 2‑pyrrolidinemethanol, 99% (S)-(+)-5-(Hydroxymethyl)- 2‑pyrrolidinone p-toluenesulfo- [207511‑15‑7] C H NO OH 649988 nate, 95% 13 17 3 CH3O N FW 235.28 O ‑ ‑ ‑ [51693 17 5] O (R)-(+)-1 Benzyl-3-(Boc-amino) C12H15NO4S S O pyrrolidine, 97% N O 345598 FW 269.32 O H H3C ‑ ‑ [131878 23 4] H ‑ ‑ N 444537 (R)-(+)-1 Benzyl-3 acetylamino- C16H24N2O2 Boc pyrrolidine, 97% FW 276.37 N

(R)-(−)-1‑Cbz-3‑aminopyrrolidine, ‑ ‑ [114636 33 8] H N CH3 97% C13H18N2O O 649961 FW 218.29 N C12H16N2O2 NH2 FW 220.27 (R)-(+)-2-(Fluorodiphenylmethyl) N Cbz pyrrolidine, 97% 536628 660078 [352535‑00‑3] (1R,2S)-1‑Phenyl-2-(1‑pyrrolidinyl)- C17H18FN ‑ ‑ ‑ FW 255.33 (S)-(+)-1 Cbz-3 aminopyrrolidine, 1 propanol, 98% N 97% H F [127641‑25‑2] 552550 C13H19NO N C12H16N2O2 NH2 FW 205.30 FW 220.27 CH3 N OH Cbz 545481 660051

14 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-(−)-2-(Fluorodiphenylmethyl) (R)-(−)-1‑Fmoc-3‑pyrrolidinol, 95% (S)-(+)-5-(Trityloxymethyl)- pyrrolidine, 97% 2‑pyrrolidinone, 98% ‑ ‑ [215178 39 5] OH [274674‑23‑6] C19H19NO3 [105526‑85‑0] N C17H18FN FW 309.36 C24H23NO2 Fmoc FW 255.33 FW 357.44 O Blocks Building Heterocyclic N N O H F 654639 H

552569 (S)-(+)-1‑Fmoc-3‑pyrrolidinol, 95% 374113 (S)-(−)-α,α-Diphenyl-2‑pyrrolidine- ‑ ‑ [215178 38 4] OH methanol, 98% C19H19NO3 (S)-(+)-N-Boc-3-N-Fmoc-amino- FW 309.36 N pyrrolidine, 97% [112068‑01‑6] Fmoc C17H19NO ‑ ‑ 654647 [307531 88 0] H FW 253.34 N OH N H C24H28N2O4 Fmoc − FW 408.49 N Methyl (2S)-( )-2-(hydroxy- Boc ‑ 552526 diphenylmethyl)-1 pyrrolidine- carboxylate, 98% 651559 − ‑ Benzyl (S)-( )-2-(1 pyrrolidinyl- [352535‑68‑3] (R)-(−)-N-Boc-3-N-Fmoc-amino- carbonyl)-1‑pyrrolidinecarboxy- C19H21NO3 pyrrolidine, 97% N late, 97% FW 311.37 HO ‑ ‑ H3CO O [352530 40 6] H ‑ ‑ N [50888 84 1] C24H28N2O4 Fmoc C17H22N2O3 N 554448 FW 408.49 N N FW 302.37 Boc Cbz O 650919 462403

Discover Super Silyl Protecting Groups

Tris(trimethylsilyl)silane (360716) won the Fluka Reagent O TTMSSO OTTMSS OTTMSS HNTf2 (0.05 mol %) of the Year award in 1990 for its use as an alternative to + H O H CH2Cl2, 1 h tributylstannane (Bu3SnH) in radical reactions. Currently, the (2.2 equiv) 75% tris(trimethylsilyl)silyl (TTMSS, or supersilyl) group is being syn:anti >95/5 utilized in carbon–carbon-bond forming reactions, where the researcher can take advantage of its unique reactivity that arises from its electronic properties and large steric bulk. Professor Hisashi Yamamoto has employed supersilyl enol ethers in a variety of efﬁ cient one-pot sequential reactions. TMS TMS OTTMSS Sigma-Aldrich is pleased to offer acetaldehyde supersilyl TMS TMS Si Si enol ether (698180) and other tris(trimethylsilyl)silyl reagents TMS H TMS Cl H that allow you to use the supersilyl protecting group in your research. 360716 409405 698180

Boxer, M. B.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 48.

For product-related inquiries, please contact our Technical Services department at 800-231-8327 (USA) or [email protected].

sigma-aldrich.com

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 15 Quinuclidines (R)-(−)-3‑Quinuclidinol hydro- (R)-(+)-3‑Aminoquinuclidine dihy- (R)-(−)-3‑Quinuclidinyl benzilate chloride, 97% drochloride, 98% ‑ ‑ [62869 69 6] O [42437‑96‑7] [123536‑14‑1] C21H23NO3 OH OH O NH2 Ph Ph C7H13NO · HCl C7H14N2 · 2HCl FW 337.41 N • HCl N • 2HCl N FW 163.65 FW 199.12 532908 415715 C003

(S)-(−)-3‑Aminoquinuclidine dihy- (2R,4S,5R)-2‑Aminomethyl-5‑ethyl- drochloride, 98% quinuclidine, ≥95.0% (GC)

[119904‑90‑4] [475160‑61‑3] H C 3 H C7H14N2 · 2HCl • 2HCl C10H20N2 N NH2 N FW 199.12 FW 168.28 H2N

415723 39867 Heterocyclic Building Blocks

Thiophenes (1R)-1-(2‑Thienyl)ethanol, ≥98.5% Boc-(R)-2-thienylglycine, 8 Boc-(R)-3-thienylglycine, 8 (GC) 97% 98% ‑ ‑ ‑ ‑ ‑ ‑ [74562 03 1] O [33130 97 1] S [86527 10 8] O CH C11H15NO4S C11H15NO4S C H OS 3 S OH 6 8 S OH FW 257.31 HN FW 257.31 FW 128.19 OH NH Boc Boc 06674 711861 711896 (1S)-1-(2‑Thienyl)ethanol, ≥98.5% Boc-(S)-2-thienylglycine, 8 Boc-(S)-3-thienylglycine, 8 (GC) 97% 98% [27948‑39‑6] [40512‑56‑9] O C11H15NO4S S CH3 O C6H8OS S C11H15NO4S S OH FW 257.31 OH FW 128.19 FW 257.31 HN OH Boc NH 00791 Boc 711853 711888

16 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Others

D-Hydroorotic acid, 98% (S)-1,4‑Benzodioxane-2‑carboxylic (3S-cis)-(+)-2,3‑Dihydro-3‑iso- acid, ≥97.0% (GC, sum of enan- propyl-7a-methylpyrrolo[2,1-b]ox- [5988‑53‑4] O tiomers) azol-5(7aH)-one, 98% C H N O Blocks Building Heterocyclic 5 6 2 4 NH FW 158.11 HO ‑ ‑ ‑ ‑ N O [70918 54 6] O [116910 11 3] CH H 3 O C H O O C H NO O 9 8 4 OH 10 15 2 FW 180.16 FW 181.23 N 537306 O O H3C CH3 ‑ 12351 (1S,4S)-(+)-2,5 Diazabicyclo[2.2.1] 458554 heptane dihydrobromide, 97% Sepiapterin ‑ ‑ (3S-cis)-(+)-Tetrahydro-3‑isopropyl- [132747 20 7] ‑ ‑ [17094 01 8] O O C5H10N2 · 2HBr HN • 2HBr 7a-methylpyrrolo[2,1-b]oxazol-5 N C9H11N5O3 H3C N FW 259.97 H N (6H)-one, 95% FW 237.22 OH N N NH2 473006 H H [98203‑44‑2] CH3 O S154 C10H17NO2 (2R,5S)-2‑Trichloromethyl-3‑oxa- FW 183.25 N O ‑ ‑ H3C 1 azabicyclo[3.3.0]octan-4 one, D-(+)-Neopterin, ≥97.5% (HPLC, CH3 ≥ 98.0% (AT) sum of enantiomers) 334235 [97538‑67‑5] ‑ ‑ H [2009 64 5] OH OH C7H8Cl3NO2 O − ‑ ‑ N C9H11N5O4 N (1S,4S)-( )-2 Boc-2,5 diazabicyclo FW 244.50 O N OH Cl3C FW 253.21 OH [2.2.1]heptane, 95% H2N NN 42134 [113451‑59‑5] N3386 C10H18N2O2 HN (+)-6‑Aminopenicillanic acid, 96% FW 198.26 N (R)-2,5‑Dihydro-3,6‑dimethoxy- Boc ‑ ≥ [551‑16‑6] 2 isopropylpyrazine, 97.0% (GC) 473049 H N H 2 S C8H12N2O3S CH3 ‑ ‑ N CH3 [109838 85 9] N OCH FW 216.26 O 3 − C9H16N2O2 ( )-p-Bromolevamisole oxalate, O OH CH3 FW 184.24 H3CO N 99% CH3 A70909 37286 O N OH (R)-(+)-1,2‑Dithiolane-3‑pentanoic Br • HO N S O acid, 97% (S)-2,5‑Dihydro-3,6‑dimethoxy- [62284‑79‑1] 2‑isopropylpyrazine, ≥97.0% (GC) [1200‑22‑2] C11H11BrN2S·C2H2O4 SOH C8H14O2S2 S [78342‑42‑4] FW 373.22 N OCH3 FW 206.33 O C H N O 190047 9 16 2 2 CH H CO N 3 579602 FW 184.24 3 CH 3 (1S,4S)-(−)-2-(4‑Chlorophenyl)- (R)-1,4‑Benzodioxane-2‑carboxylic 37289 2,5‑diazabicyclo[2.2.1]heptane acid, ≥97.0% (GC, sum of enan- hydrobromide (3R-cis)-(−)-2,3‑Dihydro-3‑iso- tiomers) ‑ ‑ propyl-7a-methylpyrrolo[2,1-b]ox- [308103 51 7] [70918‑53‑5] C11H13ClN2 · HBr NH • HBr O azol-5(7aH)-one, 98% N C H O O FW 289.60 9 8 4 OH FW 180.16 ‑ ‑ 473391 [302911 94 0] CH3 O O C10H15NO2 N CH3 12348 FW 181.23 O

CH3

458546

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 17 (1S,4S)-(−)-2-(3‑Fluorophenyl)- (1S,4S)-(+)-2‑Benzyl-2,5‑diaza- (3R-cis)-(−)-2,3‑Dihydro-7a-methyl- 2,5‑diazabicyclo[2.2.1]heptane bicyclo[2.2.1]heptane dihydrobro- 3‑phenylpyrrolo[2,1-b]oxazol-5 hydrobromide mide, 99% (7aH)-one, 98%

[294177‑35‑8] [116258‑17‑4] [302911‑95‑1] NH O C11H13FN2 · HBr HN C12H16N2 · 2HBr C13H13NO2 • HBr N FW 273.14 N FW 350.09 FW 215.25 N O F HBrHBr CH3 473030 473405 458562 − ‑ (1S,4S)-(−)-2-(4‑Fluorophenyl)- (1S,4S)-( )-2-(4 Methylphenyl)- (3S-cis)-(+)-2,3‑Dihydro-7a-methyl- ‑ 2,5‑diazabicyclo[2.2.1]heptane 2,5 diazabicyclo[2.2.1]heptane 3‑phenylpyrrolo[2,1-b]oxazol-5 hydrobromide maleate salt, 95% (7aH)-one, 98% [312624‑04‑7] [308103‑49‑3] O [143140‑06‑1] C12H16N2 ·C4H4O4 HN O C11H13FN2 · HBr HN OH C13H13NO2 • HBr N • FW 273.14 N FW 304.34 OH FW 215.25 N O Heterocyclic Building Blocks CH3 O CH3 F 495271 458570 473367 (2R,4R)-(+)-4,5‑Dihydro-4‑iso- Benzyl (S,S,S)-2‑azabicyclo[3.3.0] − ‑ ‑ propyl-2-(p-tolyl)- (4R,5S)-( )-1,5 Dimethyl-4 phenyl- 4 octane-3‑carboxylate hydro- ‑ 1,2λ ,3‑oxathiazole 2‑oxide, 98% 2 imidazolidinone, 97% chloride, 97% [170900‑87‑5] ‑ ‑ CH3 [92841 65 1] [87269‑87‑2] C12H17NO2S C11H14N2O CH3 C H NO ·HCl O • HCl FW 239.33 O N 15 19 2 FW 190.24 NH S FW 281.78 N O O H H3C N O CH3 CH3 570907 382175 648337 (−)-N-(1(R)-Phenylethyl)-1‑aza- ‑ ‑ (4S,5R)-(+)-1,5‑Dimethyl-4‑phenyl- (2S,4S)-4,5 Dihydro-4 isopropyl-2- bicyclo[2.2.2]octan-3(S)-amine di- λ4 ‑ 2‑imidazolidinone, 97% (p-tolyl)-1,2 ,3 oxathiazole hydrochloride, 98% 2‑oxide, 98% [112791‑04‑5] [128311‑06‑8] [145679‑46‑5] H C H C11H14N2O 3 C15H22N2 · 2HCl N CH FW 190.24 NH C12H17NO2S 3 FW 303.27 N CH3 • 2HCl H3C N O FW 239.33 O N S CH3 O 487244 380148 CH3 (+)-N-(1(S)-Phenylethyl)-1‑aza- (S)-(+)-2,3‑Dihydro-1H-pyrrolo[2,1- 648345 bicyclo[2.2.2]octan-3(R)-amine di- c][1,4]benzodiazepine-5,11 hydrochloride, 98% (S)-(−)-9,10‑Difluoro-2,3‑dihydro- (10H,11aH)-dione, 99% 3‑methyl-7‑oxo-7H-pyrido-[1,2,3- [120570‑09‑4] H ‑ ‑ C15H22N2 · 2HCl N [18877 34 4] O de]-1,4‑benzoxazine-6‑carboxylic FW 303.27 N C12H12N2O2 N acid, 97% CH3 • 2HCl

FW 216.24 H N ‑ ‑ 510343 H O [100986 89 8] O O C13H9F2NO4 F OH 340650 FW 281.21 Aloperine, 96% F N O CH ‑ ‑ (S)-(−)-1‑Z-2‑Oxo-5‑imidazolidine- 3 [56293 29 9] H C15H24N2 carboxylic acid, 98% N 570877 FW 232.36 ‑ ‑ H [59760 01 9] NH NH HO C12H12N2O5 N O 546704 FW 264.23 O Cbz

392308

18 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (2S-cis)-(+)-2,3‑Dihydro-3‑hydroxy- (3S-cis)-(+)-Tetrahydro-3,7a- Ergotamine D-tartrate, ≥97.0% 2-(4‑methoxyphenyl)-1,5‑benzo- diphenylpyrrolo[2,1-b]oxazol-5 (NT, calc. based on dry substance) thiazepin-4(5H)-one, 98% (6H)-one, 98% Ph ‑ ‑ ‑ ‑ O [42399 49 5] OCH3 [161970 71 4] O H C O OH O 3 N C H NO S C H NO H • ½ HO Blocks Building Heterocyclic 16 15 3 18 17 2 HN N N OH H H O FW 301.36 FW 279.33 O OH O OH N S N OH CH3 O N O [379‑79‑3] H C33H35N5O5 · 0.5C4H6O6 475548 458538 FW 656.70 45510 (+)-Usnic acid, 98% (2S)-(−)-2,2′-Oxybis(octahydro- ‑ ‑ [7562‑61‑0] OH OH O 7,8,8 trimethyl-4,7 methanobenzo- H3C C H O H3C furan), 99% 18 16 7 CH3 FW 344.32 HO OO [108031‑80‑7] H3C CH3 H3C CH3 H3C O C24H38O3 H3C FW 374.56 329967 O O H3C O H H

385298

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Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 19 Discover Unprotected Amino Aldehydes from Professor Yudin

Professor Andrei Yudin and co-workers have recently described the Unprotected Vinyl Aziridines via Olefination preparation of bench-stable, unprotected α-amino aldehydes.1 These kinetically amphoteric molecules exist as dimers, and due to the strain of H H the aziridine ring, resist inter- and intramolecular iminium ion formation. O N RH2C PPh3 Br N Furthermore, the two functionalities remain orthogonal to each other R Ph H R throughout their transformations, allowing for the reaction of the t-BuOK, THF, 3 h aldehyde without the requirement of an additional protecting group. 70-95%

OH H H O O Unprotected Vicinal 1,2-Amino Alcohols via Allylation N N N with Indium Reagents R H R R

H H O 0 Br OH N In , N Whereas the reductive amination of protected amino aldehydes has R H R significant limitations due to epimerization or overalkylation, these THF/H 2O, rt, 1 h Yudin amino aldehyde dimers do not suffer from either limitation, due 81-96% >99% diastereoselectivity to a negligible concentration of free aldehyde during the reaction. This allows the researcher facile access to a method for the creation of complex polycyclic skeletons2 or peptidomimetic conjugates3 with 4 a high degree of stereocontrol. Nucleophilic additions, Wittig and related olefination reactions can be carried out with high selectivities H H and yields. Sigma-Aldrich is pleased to offer these useful Yudin amino O O N N aldehydes for your research. H H S Cascade Polycyclizations 695556 695521

NHBn Bn N H H H H N H O O O H Ph N N TBDMSO N CF CH OH H 3 2 N H H Ph H 0 °C, 3 h N H 695513 707686 H 97% H O N H Synthesis of Peptidomimetic Conjugates Without Protecting Groups

R1 695548 NHR2 H H2N H 1 O R (1) Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 14772. (2) Yudin, A. K.; Hili, R. N O N NHR2 Chem.—Eur. J. 2007, 13, 6538. (3) Li, X.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, Ph H NaBH CN, ZnCl Ph N 3 2 H 14152. (4) Hili, R.; Yudin, A. K. Angew. Chem., Int. Ed. 2008, 47, 4188. THF/MeOH, rt O 75 - 86%

sigma-aldrich.com

misc.indd 1 6/18/2009 8:24:08 AM Organic Building Blocks

Acid Halides rai uligBlocks Building Organic (S)-(−)-2‑Acetoxypropionyl (S)-(+)-α-Methoxy-α-trifluoro- (−)-Menthoxyacetyl chloride, 97% chloride, 97% methylphenylacetyl chloride, 99% ‑ ‑ [15356 62 4] O [36394‑75‑9] [20445‑33‑4] C12H21ClO2 H3C O O H3CO CF3 Cl Cl C H ClO H3C O C H ClF O FW 232.75 CH3 5 7 3 Cl 10 8 3 2 O FW 150.56 O CH3 FW 252.62 CH3

447056 369675 453714

(R)-(−)-O-Formylmandeloyl (1S)-(+)-Menthyl chloroformate (−)-1-(9‑Fluorenyl)ethyl chloroformate solution chloride, 97% ‑ ‑ [7635 54 3] O ‑ ‑ C11H19ClO2 [154479‑90‑0] [29169 64 0] O H3C O Cl C H ClO FW 218.72 C16H13ClO2 9 7 3 H O CH3 FW 198.60 Cl FW 272.73 O CH3

O H3C O Cl 378712 479284 338710 (1R)-(−)-Menthyl chloroformate (1S)-(−)-Camphanic chloride, 98% (+)-1-(9‑Fluorenyl)ethyl chloro- [14602‑86‑9] H C CH formate solution ‑ ‑ 3 3 [39637 74 6] H C O C11H19ClO2 3 O O C10H13ClO3 H3C Cl FW 218.72 [107474‑79‑3] O Cl FW 216.66 C16H13ClO2 H C CH3 3 O FW 272.73 O

226173 245305 H3C O Cl

335975

Alcohols (S)-(+)-2‑Chloro-1‑propanol, 97% (R)-(−)-3‑Bromo-2‑methyl-1‑pro- (S)-(+)-2‑Butanol, 99% panol, 97% ‑ ‑ ‑ ‑ [19210 21 0] H C [4221 99 2] OH 3 OH C3H7ClO [93381‑28‑3] C4H10O H3C Cl Br OH CH3 FW 94.54 FW 74.12 C4H9BrO CH3 296708 FW 153.02 237698 325066 (R)-(+)-3‑Butyn-2‑ol, 98% (R)-(−)-1‑Methoxy-2‑propanol, (S)-(+)-3‑Bromo-2‑methyl-1‑pro- ≥98.5% (GC, sum of enantiomers) [42969‑65‑3] HO panol, 97% CH ‑ ‑ C4H6O [4984 22 9] OH H3C FW 70.09 ‑ ‑ OCH3 [98244 48 5] C4H10O2 H C Br OH 3 464821 FW 90.12 C4H9BrO CH3 FW 153.02 77913 (S)-(−)-3‑Butyn-2‑ol, 97% 325058 (S)-(+)-1‑Methoxy-2‑propanol, ‑ ‑ [2914 69 4] HO − ‑ ≥ CH (R)-( )-2 Butanol, 99% 98.5% (sum of enantiomers) C4H6O H3C FW 70.09 ‑ ‑ ‑ ‑ [14898 79 4] OH [26550 55 0] OH 464007 C4H10O H3C C4H10O2 OCH3 CH3 H3C FW 74.12 FW 90.12 (S)-1,4‑Dibromo-2‑butanol, ≥95.0% 236691 88808 (GC, sum of enantiomers)

‑ ‑ [64028 90 6] OH Br C4H8Br2O Br FW 231.91 77082

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 21 (R)-(−)-4‑Penten-2‑ol, 95% (R)-(−)-2,2‑Dimethyl-1,3‑dioxolane- (+)-endo-2‑Norborneol, 96% 4‑methanol, 98% ‑ ‑ ‑ ‑ [64584 92 5] OH [61277 90 5] ‑ ‑ C5H10O CH [14347 78 5] C7H12O H2C 3 OH FW 86.13 C6H12O3 OO FW 112.17 OH 558036 FW 132.16 H3C CH3 543519 (S)-(+)-4‑Penten-2‑ol, 95% 241806 (1R,2R)-trans-2‑Acetoxy-1‑cyclo- [55563‑79‑6] ‑ ‑ ≥ OH (R)-6 Chloro-2 hexanol, 98.0% pentanol, ≥99.0% (GC, sum of C5H10O H2C CH3 (GC, sum of enantiomers) enantiomers) FW 86.13 ‑ ‑ 558028 [154885 33 3] OH ‑ ‑ [105663 22 7] OH C6H13ClO Cl CH3 C7H12O3 O CH ‑ ‑ ≥ FW 136.62 FW 144.17 3 (R)-5 Chloro-2 pentanol, 95% (GC, O sum of enantiomers) 78751

Organic Building Blocks 00846 ‑ ‑ [76188 95 9] OH (S)-(+)-2‑Hexanol, 98% C H ClO Cl 5 11 CH (S)-(−)-1,1,1‑Trifluoroheptan-2‑ol, 3 [52019‑78‑0] FW 122.59 OH 97% C6H14O H3C 27618 CH3 FW 102.17 ‑ ‑ [130025 35 3] OH ‑ 655236 C7H13F3O (S)-(+)-2 Pentanol, 98% CH3(CH2)3CH2 CF3 FW 170.17 ‑ ‑ [26184 62 3] OH (S)-(+)-4‑Methyl-2‑pentanol, 98% 532525 C5H12O H3C CH3 ‑ ‑ FW 88.15 [14898 80 7] CH OH 3 (4R)-4-(2‑Hydroxyethyl)-2,2‑di- C6H14O 330515 H3C CH3 ‑ FW 102.17 methyl-1,3 dioxolane, 96% 558079 ‑ ‑ (R)-(−)-2‑Pentanol, 98% [70005 89 9] OH C7H14O3 OO ‑ ‑ [31087 44 2] OH (R)-(−)-4‑Methyl-2‑pentanol, 97% FW 146.18 H3C CH3 C5H12O H3C CH3 [16404‑54‑9] FW 88.15 H3C OH OH 331074 C6H14O 330523 H3C CH3 FW 102.17 (4S)-(+)-4-(2‑Hydroxyethyl)-2,2‑di- (S)-(−)-2‑Methyl-1‑butanol, 99% 558052 methyl-1,3‑dioxolane, 96%

‑ ‑ ‑ ‑ [1565 80 6] (R)-(−)-2‑Hexanol, 99% [32233 43 5] OH H3C OH C5H12O CH C7H14O3 3 ‑ ‑ OO FW 88.15 [26549 24 6] OH FW 146.18 H3C CH3 C6H14O H3C A83407 CH3 FW 102.17 571326 (S)-(+)-5‑Hexen-2‑ol, 97% 340308 (4S,5S)-2,2‑Dimethyl-1,3‑dioxo- ‑ ‑ [17397 24 9] OH (1S,4R)-cis-4‑Acetoxy-2‑cyclo- lane-4,5‑dimethanol, ≥97.0% H C C6H12O 2 ‑ ≥ CH3 penten-1 ol, 99% (GC, sum of enantiomers) FW 100.16 ‑ ‑ ‑ ‑ 558044 [60410 16 4] O CH [50622 09 8] 3 HO OH C7H10O3 O C7H14O4 O O FW 142.15 HO FW 162.18 (R)-(−)-5‑Hexen-2‑ol, 97% H3C CH3 446041 ‑ ‑ 59539 [17397 29 4] OH H C C6H12O 2 CH3 (1R,4S)-cis-4‑Acetoxy-2‑cyclo- (R)-(−)-2‑Heptanol, 95% FW 100.16 penten-1‑ol, ≥98.0% (GC, sum of 558060 ‑ ‑ enantiomers) [6033 24 5] OH

C7H16O CH (CH ) CH CH ‑ [60176‑77‑4] 3 2 3 2 3 (S)-(+)-1,2 Isopropylideneglycerol, H3C O OH FW 116.20 C H O 98% 7 10 3 O 408697 FW 142.15 [22323‑82‑6] OH 00848 C6H12O3 OO

FW 132.16 H3C CH3

237744

22 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-(+)-2‑Heptanol, 98% (S)-4‑Bromo-α-methylbenzyl alco- (R)-1‑Phenylethanol, 97% hol, 95% ‑ ‑ ‑ ‑ [6033 23 4] OH [1517 69 7] OH C7H16O [100760‑04‑1] C8H10O CH3(CH2)3CH2 CH3 OH CH3 FW 116.20 C8H9BrO FW 122.16 CH3

340332 FW 201.06 Blocks Building Organic Br 685828 (R)-(−)-2-[(RS)-1‑Ethoxyethoxy]- 686301 (S)-1‑Phenylethanol, 97% 1‑propanol, ≥95.0% (GC, sum of (S)-(+)-2‑Chloro-1‑phenylethanol, enantiomers) [1445‑91‑6] ≥97.0% (GC, sum of enantiomers) OH C8H10O [64028‑92‑8] CH3 CH3 FW 122.16 [70111‑05‑6] C7H16O3 OH H3C O O C8H9ClO Cl FW 148.20 OH 685836 H3C FW 156.61 17241 25905 (S)-(−)-1‑Octyn-3‑ol, 99% − α [32556‑71‑1] (R)-( )- -(Trifluoromethyl)benzyl (R)-(−)-2‑Chloro-1‑phenylethanol, HO C8H14O CH alcohol, 99% CH (CH ) CH 97% FW 126.20 3 2 3 2 ‑ ‑ [10531 50 7] OH ‑ ‑ 393967 [56751 12 3] OH C8H7F3O CF3 C8H9ClO Cl FW 176.14 FW 156.61 (R)-(+)-1‑Octyn-3‑ol, 99% 411132 ‑ ‑ 363561 [32556 70 0] HO C8H14O CH α CH3(CH2)3CH2 (S)-(+)- -(Trifluoromethyl)benzyl (R)-4‑Chloro-α-methylbenzyl alco- FW 126.20 alcohol, 99% hol, 95% 399701 ‑ ‑ [340 06 7] OH ‑ ‑ [75968 40 0] OH (R)-(+)-1,1,1‑Trifluoro-2‑octanol, C8H7F3O CF3 C8H9ClO CH3 97% FW 176.14 FW 156.61 Cl ‑ ‑ 411140 [121170 45 4] OH 686298 C8H15F3O CH3(CH2)4CH2 CF3 FW 184.20 (R)-(+)-2‑Bromo-α-methylbenzyl (S)-4‑Chloro-α-methylbenzyl alco- alcohol, 98% 537187 hol, 95% [76116‑20‑6] (S)-(−)-1,1,1‑Trifluoro-2‑octanol, OH [99528‑42‑4] C H BrO OH 8 9 CH 97% 3 C8H9ClO FW 201.06 CH3 Br FW 156.61 ‑ ‑ Cl [129443 08 9] OH 429791 C8H15F3O CH3(CH2)4CH2 CF3 686271 FW 184.20 (S)-(−)-2‑Bromo-α-methylbenzyl 532533 (S)-4‑Fluoro-α-methylbenzyl alco- alcohol, 98% hol, 97% (S)-1‑Octen-3‑ol, ≥95% (HPLC, sum [114446‑55‑8] OH [101219‑73‑2] of enantiomers) C8H9BrO OH CH3 C8H9FO FW 201.06 CH3 [24587‑53‑9] Br FW 140.15 OH F C8H16O CH2 CH3(CH2)3CH2 327247 FW 128.21 685852 40577 (R)-4‑Bromo-α-methylbenzyl alco- (R)-4‑Fluoro-α-methylbenzyl alcohol, 95% ‑ ‑ hol, 97% (R)-(+)-1 Fluoro-2 octanol, 97% ‑ ‑ [76155 78 7] OH [110270‑42‑3] ‑ ‑ CH3(CH2)4CH2 [101219 68 5] F C8H9BrO OH CH3 C8H17FO C8H9FO OH FW 201.06 CH3 Br FW 140.15 FW 148.22 F 477362 686336 685844

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 23 (R)-(−)-2‑Octanol, 99% (R)-(−)-1‑Indanol, 99% (R)-(+)-1‑Phenyl-1‑propanol, 99%

‑ ‑ ‑ ‑ ‑ ‑ [5978 70 1] OH [697 64 3] OH [1565 74 8] OH C8H18O C9H10O C9H12O CH3 CH3(CH2)4CH2 CH3 FW 130.23 FW 134.18 FW 136.19 147990 328413 256331 (S)-(+)-2‑Octanol, 99% ‑ ‑ ‑ ≥ (S)-1 Phenyl-2 propen-1 ol, 97.0% (S)-(−)-1‑Phenyl-1‑propanol, 99% [6169‑06‑8] (GC, sum of enantiomers) OH ‑ ‑ [613 87 6] OH C8H18O CH (CH ) CH CH ‑ ‑ 3 2 4 2 3 [39623 35 3] OH C9H12O CH3 FW 130.23 CH C9H10O 2 FW 136.19 147982 FW 134.18 256323 (S)-(+)-3‑Octanol, 97% 78974 − ‑ ‑ ‑ ‑ (R)-( )-1 Phenyl-2 propanol, Organic Building Blocks [22658 92 0] ‑ ‑ ‑ ≥ OH (R)-1 Phenyl-2 propen-1 ol, 95% ≥97.0% (GC, sum of enantiomers) C8H18O CH3 H3C (GC, sum of enantiomers) FW 130.23 [1572‑95‑8] ‑ ‑ CH3 666718 [104713 12 4] OH C9H12O OH CH C9H10O 2 FW 136.19 FW 134.18 (R)-1‑Phenyl-2‑propyn-1‑ol, ≥99.0% 78926 (GC, sum of enantiomers) 78972 ‑ ‑ ‑ ‑ (R)-(+)-2 Phenyl-1 propanol, 98% [61317 73 5] OH (S)-(−)-3‑Chloro-1‑phenyl-1‑pro- C9H8O CH [19141‑40‑3] panol, 98% CH3 FW 132.16 C9H12O OH ‑ ‑ FW 136.19 78976 [100306 34 1] OH C H ClO 9 11 Cl 461407 (S)-1‑Phenyl-2‑propyn-1‑ol, ≥99.0% FW 170.64 − ‑ ‑ (GC, sum of enantiomers) 324612 (S)-( )-2 Phenyl-1 propanol, 98% [64599‑56‑0] [37778‑99‑7] OH CH3 CH ‑ ‑ ‑ C9H8O (R)-(+)-3 Chloro-1 phenyl-1 pro- C9H12O OH FW 132.16 panol, 98% FW 136.19 ‑ ‑ 78978 [100306 33 0] OH 461415

C9H11ClO Cl (S)-(−)-1‑Chloro-3-(4‑fluorophen- FW 170.64 (S)-(+)-1‑Phenyl-2‑propanol, oxy)-2‑propanol, 97% ≥ 338419 97.0% (GC, sum of enantiomers) [352530‑45‑1] [1517‑68‑6] OH CH3 C H ClFO O Cl (S)-(+)-1-(4‑Fluorophenoxy)-2‑pro- 9 10 2 C9H12O OH FW 204.63 F panol, 97% FW 136.19 ‑ ‑ 78927 537128 [206125 75 9] OH C9H11FO2 O CH3 ‑ ‑ FW 170.18 (S)-(+)-2 Methoxy-2 phenyl- (R)-(+)-1‑Chloro-3-(4‑fluorophen- F ‑ ethanol, 98% oxy)-2 propanol, 97% 537098 [66051‑01‑2] ‑ ‑ OCH3 [307532 04 3] OH (R)-(−)-1-(4‑Fluorophenoxy)-2‑pro- C9H12O2 OH C9H10ClFO2 O Cl FW 152.19 FW 204.63 panol, 97% F 302147 ‑ ‑ 537101 [307532 03 2] OH C9H11FO2 O CH3 (R)-(−)-2‑Methoxy-2‑phenyl- ‑ FW 170.18 (S)-(+)-1 Indanol, 99% F ethanol, 98% ‑ ‑ 537071 [25501 32 0] OH ‑ ‑ [17628 72 7] OCH C H O 3 9 10 C9H12O2 OH FW 134.18 FW 152.19 323128 302775

24 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. D-α,β-Cyclohexylideneglycerol, (S)-(+)-4‑Phenyl-2‑butanol, 98% (−)-trans-Pinocarveol, ≥96.0% (GC, ≥98.0% (GC, sum of enantiomers) sum of enantiomers) ‑ ‑ [22148 86 3] OH ‑ ‑ [95335‑91‑4] C10H14O CH [547 61 5] O 3 CH3 C9H16O3 FW 150.22 C10H16O H C CH2 O OH 3 OH FW 172.22 FW 152.23 Blocks Building Organic 558095 29400 (R)-(−)-4‑Phenyl-2‑butanol, 98% 80613 (S)-(+)-2‑Nonanol, 97% [39516‑03‑5] ‑ ‑ OH (S)-cis-Verbenol, 95% [70419 06 6] OH C10H14O CH3 C9H20O H C CH ‑ ‑ 3 3 FW 150.22 [18881 04 4] CH FW 144.25 3 C10H16O H C 557978 558109 FW 152.23 3 H3C OH

(R)-(−)-2‑Nonanol, 97% (R)-(−)-1‑Benzyloxy-2‑propanol, 247065 97% [70419‑07‑7] OH (+)-Borneol, 97% C9H20O [89401‑28‑5] H3C CH3 OH FW 144.25 C10H14O2 O ‑ ‑ H C [464 43 7] CH FW 166.22 3 H3C 3 557951 C10H18O 650846 FW 154.25 ‑ H C (R)-1-[3,5 Bis(trifluoromethyl)phe- 3 OH nyl]ethanol, ≥98.0% (GC) (S)-(+)-1‑Benzyloxy-2‑propanol, 97% 420247 ‑ ‑ [127852 28 2] OH C10H8F6O F3C [85483‑97‑2] (−)-Borneol, 97% CH3 OH FW 258.16 C10H14O2 O H3C ‑ ‑ [464 45 9] CH CF3 FW 166.22 H3C 3 C H O CH 650838 10 18 3 49554 FW 154.25 OH (R)-Glycerol 1-(p-toluenesulfo- (S)-(+)-1,2,3,4‑Tetrahydro-1‑naph- 139114 nate), 95% (TLC) thol, 99% − [41274‑09‑3] (1S,2S,5S)-( )-Myrtanol, 97% [53732‑47‑1] O OH C10H14O5S S O OH ‑ ‑ C10H12O [53369 17 8] H C CH FW 246.28 O OH 3 3 FW 148.20 H3C C10H18O FW 154.25 H G2410 256293 OH

− 274178 (R)-(−)-1,2,3,4‑Tetrahydro-1‑naph- (S)-( )-Perillyl alcohol, 96% thol, 99% [18457‑55‑1] OH (1R)-endo-(+)-Fenchyl alcohol, 96% C H O [23357‑45‑1] 10 16 H2C OH FW 152.23 [2217‑02‑9] C H O CH3 10 12 C H O FW 148.20 10 18 CH3 218391 FW 154.25 CH3 H3C 256285 OH − (1R)-( )-Myrtenol, 95% 196444 (R)-(+)-1‑Phenyl-1‑butanol, 97% [19894‑97‑4] H C 3 CH3 (+)-Dihydrocarveol, ≥95.0% ‑ ‑ C10H16O [22144 60 1] OH FW 152.23 (GC, sum of enantiomers) C10H14O CH3 OH FW 150.22 ‑ ‑ [22567 21 1] CH 188417 3 C10H18O 317314 H2C FW 154.25 OH (−)-Carveol, mixture of isomers, CH3 (S)-(−)-1‑Phenyl-1‑butanol, 97% 97% 37277 ‑ ‑ [22135 49 5] OH ‑ ‑ [99 48 9] CH3 C10H14O CH3 C10H16O H C FW 150.22 2 OH FW 152.23 CH3 317322 192384

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 25 (−)-Dihydrocarveol, ≥95.0% (1S,2S,3S,5R)-(+)-Isopinocampheol, (R)-(−)-2‑Decanol, 97% (GC, sum of enantiomers) 98% ‑ ‑ [33758 15 5] OH [20549‑47‑7] [27779‑29‑9] C10H22O CH3 CH3 CH3(CH2)6CH2 CH3 C10H18O C10H18O OH FW 158.28 H2C OH FW 154.25 FW 154.25 H3C 557986 CH3 H3C 37278 250856 (S)-3‑Butene-1,2‑diol-1-(p-toluenesulfonate), ≥99.0% (HPLC) (+)-Isopulegol, 99% − (1R,2R,3R,5S)-( )-Isopinocampheol, ‑ ‑ [133095 74 6] O [104870‑56‑6] 98% S O CH3 C11H14O4S CH2 O OH C10H18O FW 242.29 H2C [25465‑65‑0] H C FW 154.25 CH3 3 CH3 OH C10H18O OH 19163 FW 154.25 H3C 439053 H3C

Organic Building Blocks (R)-3‑Butene-1,2‑diol-1-(p-toluene- − 221902 ( )-Isopulegol, 99% sulfonate), ≥99.0% (HPLC) ‑ ‑ [89 79 2] CH ‑ ‑ ‑ 3 (1S,2S,4R)-(+)-Limonene-1,2 diol, [138249 07 7] O C10H18O H2C ≥97.0% (GC) C11H14O4S S O CH2 FW 154.25 O OH CH3 OH FW 242.29 [38630‑75‑0] H3C CH3 439061 C10H18O2 OH 19162 H C FW 170.25 2 OH − ≥ CH3 ( )-Linalool, 95.0% (GC, sum of (1R)-(−)-Nopol, 98% enantiomers) 669768 [35836‑73‑8] ‑ ‑ H3C CH3 [126 91 0] CH C H O 3 H3C OH (R)-(+)-β-Citronellol, 98% 11 18 C10H18O CH2 H3C FW 166.26 FW 154.25 [1117‑61‑9] OH CH3 CH3 62139 C10H20O 340367 H3C OH FW 156.27 α-Terpineol, 90% 303461 2‑Methylisoborneol solution, ≥98% (GC) [10482‑56‑1] CH3 (S)-(−)-β-Citronellol, 99% C10H18O ‑ ‑ H3C [2371 42 8] CH FW 154.25 H3C 3 H C OH [7540‑51‑4] 3 H3C OH C11H20O C10H20O FW 168.28 OH CH3 CH3 432628 H3C FW 156.27 CH3 303488 (−)-Terpinen-4‑ol, ≥95.0% (GC, sum M3933 of enantiomers) (1R,2S,5R)-(−)-Menthol, 99% (R)-(+)-α−Methyl-1‑naphthalene- [20126‑76‑5] CH3 ‑ ‑ methanol, 99% [2216 51 5] H3C OH C10H18O C10H20O FW 154.25 CH3 [42177‑25‑3] FW 156.27 H3C OH CH3 HO CH3 C12H12O H3C M2780 FW 172.22 11584 (1S,2R,5S)-(+)-Menthol, 99% 372315 Isoborneol, 95% ‑ ‑ − α− ‑ [15356 60 2] H C OH (S)-( )- Methyl-1 naphthalene- ‑ ‑ 3 [124 76 5] H C CH C10H20O 3 3 CH3 methanol, 99% C10H18O CH3 FW 156.27 OH CH 3 [15914‑84‑8] FW 154.25 H3C OH 224464 C12H12O I13901 FW 172.22 (1S,2S,5R)-(+)-Neomenthol, 97% 372323 ‑ ‑ [2216 52 6] H3C OH C10H20O CH3 FW 156.27 CH3

235180

26 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (R)-(+)-1-(2‑Naphthyl)ethanol, 98% (1S,2R)-(+)-trans-2-(1‑Methyl- (S)-(−)-1‑Phenyl-1‑decanol, 95% 1‑phenylethyl)cyclohexanol, 98% ‑ ‑ ‑ ‑ [52193 85 8] OH [112419 76 8] OH C12H12O [109527‑45‑9] C16H26O CH3 OH CH3 CH3(CH2)7CH2 FW 172.22 C15H22O FW 234.38 CH3 FW 218.33 Blocks Building Organic 346217 331619 453404 (S)-(−)-α−Methyl-2‑naphthalene- (S)-(−)-2,3‑Dibenzyloxy-1‑propanol, methanol, 98% (1R,2S)-(−)-trans-2-(1‑Methyl- 96% 1‑phenylethyl)cyclohexanol, 98% [27544‑18‑9] [20196‑71‑8] OH Ph O OH C12H12O [109527‑43‑7] C17H20O3 O Ph CH3 OH CH3 FW 172.22 C15H22O FW 272.34 FW 218.33 CH3 526150 323144 453390 (S)-2‑Benzyloxy-1,3‑propanediol 1- (1R,2S)-trans-2‑Phenyl-1‑cyclo- (p-toluenesulfonate), ≥99.0% hexanol, 99% − ( )-Guaiol, 97% (HPLC, sum of enantiomers) [98919‑68‑7] [489‑86‑1] CH3 ‑ ‑ OH [109371 30 4] OH C H O C H O O 12 16 15 26 C H O S 17 20 5 S O FW 176.25 FW 222.37 O H3C FW 336.40 O CH3 H3C H3C 367249 OH 13746 448575 (1S,2R)-(+)-trans-2‑Phenyl-1‑cyclo- − ‑ hexanol, 99% (R)-(−)-1-(9‑Anthryl)-2,2,2‑trifluoro- (R)-( )-1 Benzyloxy-3-(p-tosyloxy)- ‑ ethanol, ≥98% 2 propanol, 95% [34281‑92‑0] OH C12H16O [53531‑34‑3] O HO CF3 FW 176.25 H3C S O O C16H11F3O O OH FW 276.25 367257 [23214‑66‑6] C H O S 211354 17 20 5 (S)-(−)-1,1,1,2,2‑Pentafluoro- FW 336.40 dodecan-3‑ol, 97% (S)-(+)-1-(9‑Anthryl)-2,2,2‑trifluoro- 364886 ≥ ‑ ‑ ethanol, 98% [307531 78 8] OH (R)-(+)-1-(2,4,6‑Triisopropylphenyl) C12H21F5O CH3(CH2)7CH2 CF2CF3 [60646‑30‑2] ethanol, ≥96.0% (HPLC) FW 276.29 HO CF3 C16H11F3O ‑ ‑ 532517 FW 276.25 [181531 14 6] i-Pr OH C17H28O CH3 FW 248.40 (S)-(−)-1-(9‑Fluorenyl)ethanol, 211346 i-Pr i-Pr ≥99.0% (HPLC) 672599 (−)-8‑Phenylmenthol, 98% [151775‑20‑1] C15H14O [65253‑04‑5] CH3 OH H3C FW 210.27 C16H24O H3C OH FW 232.36 CH3 00925 329487 (S)-(+)-1‑Phenyl-1,2‑ethanediol ‑ ≥ 2‑tosylate, 98% (+)-8 Phenylmenthol, 98.0% (HPLC, sum of enantiomers) ‑ ‑ [40435 14 1] O OH [57707‑91‑2] C H O S H3C S O CH3 OH 15 16 4 H3C FW 292.35 O C16H24O FW 232.36 CH3 317853 78803

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 27 (S)-(−)-1-(2,4,6‑Triisopropylphenyl) (1R,2S,4R)-(−)-4-(1‑Methylethyl)-2- (4aR)-trans-5-(1,5,5,8aS-Tetra- ethanol, ≥98.5% (HPLC) (1‑methyl-1‑phenylethyl)cyclo- methyl-2‑methylenedecahydro- hexanol, 98% 1‑naphthalenyl)-(3R)-methyl- [102225‑88‑7] i-Pr OH 1‑penten-3‑ol, 98% C17H28O [167752‑95‑6] CH3 OH FW 248.40 C18H28O [596‑85‑0] i-Pr i-Pr H3C CH2 FW 260.41 C H O H3C HO CH3 CH H3C CH3 20 34 CH2 672483 3 FW 290.48 H 453412 H C CH (1S,2R,4S)-(+)-4-(1‑Methylethyl)-2- 3 3 (1‑methyl-1‑phenylethyl)cyclo- (4bS)-trans-8,8‑Trimethyl- 532665 hexanol, 98% 4b,5,6,7,8,8a,9,10‑octahydro-1‑iso- ‑ ≥ propylphenanthren-2‑ol, 98% 2,3 Dilauroyl-sn-glycerol, 99.0% (CH3)2CHC6H9[C(CH3) OH (TLC) 2C6H5]OH ‑ ‑ H3C [511 15 9] OH ‑ ‑ H C CH C20H30O H3C [61475 84 1] CH3 3 3 CH3 O Organic Building Blocks FW 286.45 C27H52O5 CH3 H3C(H2C)10 O OH 453420 H FW 456.70 O O H3C CH3 (CH2)10CH3 532657 38481

Aldehydes (R)-(+)-2,2‑Dimethyl-1,3‑dioxolane- (−)-Myrtenal, ≥97.0% (GC, sum of (S)-(−)-Perillaldehyde, 92% 4‑carboxaldehyde enantiomers) ‑ ‑ [18031 40 8] O [15186‑48‑8] [18486‑69‑6] C10H14O O H C H 3 CH3 FW 150.22 H2C C6H10O3 H C10H14O

FW 130.14 O O FW 150.22 CH3 O H3C CH3 H 218294 454486 70125 (R)-(+)-Citronellal, 90% (R)-1,4‑Dioxaspiro[4.5]decane- (+)-Perillaaldehyde, ≥98.0% [2385‑77‑5] 2‑carboxaldehyde CH3 CH3 O (GC, sum of enantiomers) C10H18O H3C H [78008‑36‑3] FW 154.25 O ‑ ‑ [5503 12 8] O C9H14O3 343641 O H C10H14O H FW 170.21 O FW 150.22 H2C (S)-(−)-Citronellal, 96% 543039 CH3 [5949‑05‑3] 77301 CH3 CH3 O (1R)-(−)-Myrtenal, 98% C10H18O H3C H FW 154.25 [18486‑69‑6] H C 3 CH3 373753 C10H14O FW 150.22 O H

218243

28 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Amides

(R)-(+)-Lactamide, 97% (+)-N,N,N′,N′-Tetramethyl-L-tartaric (+)-N,N′-Dibenzyl-L-tartaric acid diamide, 98% diamide, 99% ‑ ‑ [598 81 2] O C3H7NO2 H3C [26549‑65‑5] [88393‑56‑0] Blocks Building Organic NH2 O OH CH3 O OH OH H FW 89.09 C8H16N2O4 H3C N C18H20N2O4 N N CH3 N FW 204.22 CH OH O FW 328.36 H 436801 3 OH O

376418 276057 (S)-(−)-Lactamide, 97% 2,2,2‑Trifluoro-N-[(S)-α-methyl- [89673‑71‑2] (−)-N,N′-Dibenzyl-D-tartaric O benzyl]acetamide, 99% C3H7NO2 H3C diamide, 99% NH2 FW 89.09 OH [39995‑51‑2] CH3 O [108321‑43‑3] O OH 436828 C10H10F3NO H N CF3 C18H20N2O4 N H N FW 217.19 H FW 328.36 OH O (S)-(+)-2‑Aminobutanamide hydro- 399779 chloride, 97% 276065 ‑ ‑ (+)-N,N′-Diallyltartramide, ≥99% [7682 20 4] O (R)-(−)-N-[1-(1‑Naphthyl)ethyl]- C4H11ClN2O ‑ H3C NH2 [58477‑85‑3] 3,5 dinitrobenzamide, 97% OH O FW 138.60 NH2 • HCl H C10H16N2O4 N CH2 H2C N ‑ ‑ H [85922 30 1] 679399 FW 228.25 O OH C19H15N3O5 O 156868 FW 365.34 O2N – ‑ N CH3 (R)-( )-2 Aminobutanamide hydro- H chloride, 97% − ‑ ‑ (R)-( )-3,5 Dinitro-N-(1 phenyl- NO2 [103765‑03‑3] ethyl)benzamide, 98% O 461601 C4H11ClN2O H3C NH2 [69632‑32‑2] O CH3 FW 138.60 NH2 • HCl O N C15H13N3O5 2 N (S)-(+)-N-[1-(1‑Naphthyl)ethyl]- H 679380 FW 315.28 3,5‑dinitrobenzamide, 97%

NO2 − ‑ [85922‑31‑2] (R)-( )-2,2 Dimethylcyclopropane- 296902 C19H15N3O5 1‑carboxamide, 97% O FW 365.34 O2N ‑ ‑ N CH3 ‑ ‑ (S)-(+)-3,5 Dinitro-N-(1 phenyl- H [106462 18 4] O C6H11NO ethyl)benzamide, 98% NH2 NO2 FW 113.16 H3C CH3 [69632‑31‑1] O CH3 461628 C15H13N3O5 O2N 679410 N FW 315.28 H (−)-O,O′-Dibenzoyl-L-tartaric acid NO (S)-(+)-2,2‑Dimethylcyclopropane- 2 mono(dimethylamide), ≥99.0% (T) 296910 carboxamide, 98% ‑ ‑ [78761 37 2] O O HO [75885‑58‑4] C20H19NO7 O α-Oxo-N-[(R)-1‑phenylethyl] O FW 385.37 O C6H11NO NH2 phenylacetamide, 98% O FW 113.16 O N H3C CH3 H C CH3 [10549‑15‑2] 3 O H 434639 C16H15NO2 N 33624 FW 253.30 O CH3 N,N,N′,N′-Tetramethyl-D-tartar- amide, 98% 422290

[63126‑52‑3] O OH CH3 C8H16N2O4 H3C N N CH3 FW 204.22 CH3 OH O

376396

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 29 Amines (S)-(+)-sec-Butylamine, 99% (S)-2‑Aminohexane, ≥97.0% (GC) (S)-4‑Chloro-α-methylbenzylamine, ≥95.0% (GC) [513‑49‑5] [70492‑67‑0] NH2 NH2 C4H11N H3C C6H15N H3C [4187‑56‑8] CH3 CH3 NH2 FW 73.14 FW 101.19 C8H10ClN CH3 296651 77914 FW 155.62 Cl

(R)-(−)-sec-Butylamine, 99% (R)-2‑Aminohexane, ≥97.0% (GC) 19506

[13250‑12‑9] [70095‑40‑8] α ‑ NH2 NH2 (R)- -Methyl-4 nitrobenzylamine C4H11N H3C C6H15N H3C CH3 CH3 hydrochloride, 97% FW 73.14 FW 101.19 [57233‑86‑0] 296643 30192 CH3 C8H10N2O2 · HCl NH2 • HCl Organic Building Blocks − − ‑ FW 202.64 (S)-( )-sec-Butylamine hydro- (R)-( )-2 Aminoheptane, 99% O2N chloride, ≥98.0% (AT) [6240‑90‑0] 339814 NH2 C7H17N C4H11N · HCl NH2 H3C CH3 • HCl FW 109.60 H3C FW 115.22 (S)-α-Methyl-4‑nitrobenzylamine CH3 462624 hydrochloride, 97% 94212 [132873‑57‑5] (S)-(+)-2‑Aminoheptane, 99% CH3 − ‑ C8H10N2O2 · HCl (S)-( )-2 Methylbutylamine, 95% NH2 ‑ ‑ FW 202.64 [44745 29 1] NH • HCl ‑ ‑ 2 O2N [34985 37 0] C7H17N H3C NH2 H3C CH3 C5H13N CH3 FW 115.22 339822 FW 87.16 462632 241407 (R)-(+)-α-Methylbenzylamine, 98% − ‑ (S)-( )-1-(4 Bromophenyl)ethyl- ‑ ‑ ‑ ‑ [3886 69 9] NH (S)-(+)-2 Amino-3 methylbutane, amine, ≥98.0% (GC, sum of enan- 2 C8H11N ≥98.0% (GC) CH3 tiomers) FW 121.18 [22526‑46‑1] NH2 [27298‑97‑1] NH2 115541 C5H13N H3C CH3 C8H10BrN CH3 FW 87.16 CH3 FW 200.08 Br (S)-(−)-α-Methylbenzylamine, 98% 91936 18072 [2627‑86‑3] NH2 C8H11N (R)-(−)-2‑Amino-3‑methylbutane, CH3 (R)-(+)-1-(4‑Bromophenyl)ethyl- FW 121.18 ≥97.0% (GC) amine, ≥96.0% (GC, sum of enan- 115568 [34701‑33‑2] tiomers) NH2 C5H13N H3C CH3 ‑ ‑ [45791 36 4] NH (R)-(−)-1‑Cyclohexylethylamine, FW 87.16 CH3 2 C8H10BrN CH3 98% 18241 FW 200.08 Br [5913‑13‑3] NH2 ‑ ‑ 18069 C8H17N (S)-(+)-3,3 Dimethyl-2 butylamine, CH3 97% FW 127.23 (R)-4‑Chloro-α-methylbenzylamine, 336505 [22526‑47‑2] ≥ H3C NH2 95.0% (GC) C6H15N H3C CH H3C 3 [27298‑99‑3] (S)-(+)-1‑Cyclohexylethylamine, FW 101.19 NH2 C8H10ClN 98% 668516 CH3 FW 155.62 Cl [17430‑98‑7] − ‑ ‑ NH2 (R)-( )-3,3 Dimethyl-2 butylamine, C8H17N 18196 CH3 97% FW 127.23

[66228‑31‑7] 336513 H3C NH2 C6H15N H3C CH FW 101.19 H3C 3 668427

30 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (R)-2‑Aminooctane, ≥98.0% (GC) (R)-(+)-N,α-Dimethylbenzylamine, (R)-(−)-1,2,3,4‑Tetrahydro-1‑naph- 98% thylamine, 97% [34566‑05‑7] NH2 C8H19N H3C [5933‑40‑4] [23357‑46‑2] CH3 CH3 NH2 FW 129.24 CH C9H13N N 3 C10H13N H 93786 FW 135.21 FW 147.22 Blocks Building Organic

394009 668818 (S)-2‑Aminooctane, ≥97.0% (GC)

[34566‑04‑6] (S)-(−)-N,α-Dimethylbenzylamine, (S)-(−)-N,N-Dimethyl-1‑phenyl- NH2 C8H19N H3C 98% CH3 ethylamine, 97% FW 129.24 [19131‑99‑8] [17279‑31‑1] 05023 CH3 CH3 C H N CH3 CH3 9 13 N C10H15N N H FW 135.21 FW 149.23 CH (S)-(+)-1‑Aminoindan, 97% 3 401358 242063 [61341‑86‑4] C H N 9 11 (R)-(+)-α,4‑Dimethylbenzylamine, (R)-(+)-N,N-Dimethyl-1‑phenyl- FW 133.19 NH 2 98% ethylamine, 97% 445355 [4187‑38‑6] [19342‑01‑9] NH2 CH3 C9H13N C10H15N CH3 (R)-(−)-1‑Aminoindane, 97% CH3 N FW 135.21 FW 149.23 CH3 H3C [10277‑74‑4] 405248 242071 C9H11N

FW 133.19 NH2 (R)-(+)-β-Methylphenethylamine, (S)-(+)-α-(Methoxymethyl)phen- 445347 99% ethylamine hydrochloride, 98% − α ‑ ‑ ‑ [64715‑81‑7] (S)-( )- ,4 Dimethylbenzylamine, [28163 64 6] CH OCH3 • HCl 3 C H NO · HCl 98% C9H13N NH2 10 15 NH2 FW 135.21 FW 201.69 [27298‑98‑2] NH2 459275 461385 C9H13N CH3 FW 135.21 H C (R)-(+)-Bornylamine, 97% 3 (S)-(−)-4‑Methoxy-α-methylbenzyl- ‑ ‑ 405256 amine, ≥98.0% (GC, sum of enan- [32511 34 5] CH H3C 3 tiomers) C10H19N (S)-β-Methylphenethylamine, 99% FW 153.26 H3C [41851‑59‑6] NH2 NH2 ‑ ‑ [17596 79 1] CH C9H13NO 3 CH3 359939 C9H13N NH2 FW 151.21 H3CO FW 135.21 − 95889 (1R,2R,3R,5S)-( )-Isopinocampheyl- 461393 amine, 95%

(R)-(+)-4‑Methoxy-α-methylbenzyl- ‑ ‑ − α [69460 11 3] CH (S)-( )- -Ethylbenzylamine, amine, ≥95.0% (GC) 3 ≥ C10H19N NH2 95.0% (GC) H3C ‑ ‑ FW 153.26 [22038 86 4] NH H3C [3789‑59‑1] 2 NH2 C9H13NO CH3 C9H13N CH3 FW 151.21 391654 FW 135.21 H3CO 18159 (1S,2S,3S,5R)-(+)-Isopinocampheyl- 51432 amine, 95% (S)-(+)-1,2,3,4‑Tetrahydro-1‑naph- (R)-(+)-α-Ethylbenzylamine, [13293‑47‑5] thylamine, 97% CH3 ≥99.0% (GC) C10H19N NH2 H C ‑ ‑ FW 153.26 3 [23357 52 0] NH [3082‑64‑2] 2 H3C NH2 C10H13N C9H13N CH3 FW 147.22 391662 FW 135.21

668796 50282

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 31 (−)-cis-Myrtanylamine, 98% (R)-(+)-1-(1‑Naphthyl)ethylamine (S)-(−)-N,N-Dimethyl-1-(1‑naph- hydrochloride, 97% thyl)ethylamine, 97% [38235‑68‑6] C10H19N [82572‑04‑1] [121045‑73‑6] H3C NH2 CH3 H3C FW 153.26 CH3 C12H14ClN C14H17N H3C N NH2 • HCl CH3 FW 207.70 FW 199.29 180807 656755 (R)-(−)-Isobornylamine hydro- 461504 chloride, ≥97.0% (AT) (S)-(−)-1-(1‑Naphthyl)ethylamine ‑ hydrochloride, 97% (R)-(+)-N,N-Dimethyl-1-(1 naph- [24629‑78‑5] CH3 thyl)ethylamine, 96% H3C C10H19N · HCl CH3 ‑ ‑ H2N [51600 24 9] H C NH 3 2 [119392‑95‑9] FW 189.73 HCl C12H14ClN CH3 • HCl C14H17N H3C N H FW 207.70 CH3 FW 199.29 58335

Organic Building Blocks 656747 (R)-(+)-N-allyl-α-methylbenzyl- 461490 (1S,2S)-trans-2‑Benzyloxycyclo- amine, 97% pentylamine, 98% (R)-1,1‑Diphenyl-1‑fluoro-2‑amino- [126275‑19‑2] CH3 [181657‑57‑8] propane, 97% NH2 C11H15N CH2 N C H NO H 12 17 FW 161.24 O C15H16FN FW 191.27 NH FW 229.29 2 CH 559032 F 3 671649 (R)-(+)-1-(1‑Naphthyl)ethylamine, (R)-(+)-N-Methyl-1-(1‑naphthyl) ≥99% 549525 ethylamine, 97% [3886‑70‑2] H3C NH2 ‑ ‑ ‑ [15297‑33‑3] (S)-1,1 Diphenyl-1 fluoro-2 amino- C12H13N H H3C N propane, 97% FW 171.24 C13H15N CH3 FW 185.26 C15H16FN NH 237442 FW 229.29 2 CH 461474 F 3 (S)-(−)-1-(1‑Naphthyl)ethylamine, ≥99% (S)-(−)-N-Methyl-1-(1‑naphthyl) ethylamine, 97% 549533 [10420‑89‑0] H3C NH2 C H N ‑ ‑ 12 13 [20218 55 7] H (R)-(+)-1,1‑Diphenyl-2‑amino- H C N FW 171.24 C H N 3 CH 13 15 3 propane, 97% FW 185.26 237450 C15H17N NH2 461482 FW 211.30 (R)-(+)-1-(2‑Naphthyl)ethylamine, CH3 ≥ 99.0% (GC, sum of enantiomers) (4S,5S)-(+)-2,2‑Dimethyl-5‑methyl- ‑ ‑ [3906‑16‑9] amino-4 phenyl-1,3 dioxane, 549495 NH2 ≥ C12H13N 98.0% (GC, sum of enantiomers) CH3 FW 171.24 − ‑ ‑ [124686‑47‑1] (S)-( )-1,1 Diphenyl-2 amino- propane, 97% 70940 C13H19NO2 FW 221.30 H N [67659‑37‑4] H3C O (S)-(−)-1-(2‑Naphthyl)ethylamine, NH2 CH3 C15H17N O CH ≥99.0% (GC, sum of enantiomers) CH3 FW 211.30 3

[3082‑62‑0] 40767 NH2 C12H13N CH3 549487 FW 171.24

70942

32 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-(−)-N-Benzyl-α-methylbenzyl- (R)-(+)-2‑Amino-1‑fluoro-3‑methyl- (R)-(+)-2‑Amino-4‑methyl- amine, 99% 1,1‑diphenylbutane, 97% 1,1‑diphenylpentane, 98%

‑ ‑ ‑ ‑ [17480 69 2] CH C17H20FN [352535 73 0] 3 NH2 CH3 NH2 C15H17N FW 257.35 H3C C18H23N N H3C H F FW 211.30 CH3 FW 253.38 Blocks Building Organic

427470 551090 554618 (R)-(+)-N-Benzyl-α-methylbenzylamine, 98% (S)-(−)-2‑Amino-3‑methyl- (S)-(−)-2‑Amino-4‑methyl- 1,1‑diphenylbutane, 98% 1,1‑diphenylpentane, 97% [38235‑77‑7] CH3 C15H17N [233772‑37‑7] [233772‑40‑2] N CH NH FW 211.30 H NH2 3 2 C17H21N H3C C18H23N H3C FW 239.36 CH FW 253.38 431737 3

‑ (+)-Bis[(R)-1 phenylethyl]amine, 551147 554626 99% ‑ ‑ (R)-(−)-N-Benzyl-1-(1‑naphthyl) [23294‑41‑9] (R)-(+)-2 Amino-3 methyl- CH3 CH3 ‑ C H N 1,1 diphenylbutane, 98% ethylamine hydrochloride, 98% 16 19 N FW 225.33 H [400870‑29‑3] [163831‑65‑0] NH2 H C19H19N · HCl N 452823 C17H21N H3C H3C FW 297.82 FW 239.36 CH3 • HCl (−)-Bis[(S)-1‑phenylethyl]amine, 99% 551155 445959 [56210‑72‑1] CH3 CH3 C H N (S)-(−)-2‑Amino-1‑fluoro-4‑methyl- (S)-N-Benzyl-1-(1‑naphthyl)ethyl- 16 19 N FW 225.33 H 1,1‑diphenylpentane, 98% amine hydrochloride, ≥96.0% (AT)

433810 [274674‑22‑5] [163831‑66‑1] CH 3 NH2 H C18H22FN C19H19N · HCl H3C N H C ‑ FW 271.37 3 F FW 297.82 (+)-Bis[(R)-1 phenylethyl]amine • HCl hydrochloride, 97%

[82398‑30‑9] 554642 13597 CH3 CH3 C16H19N · HCl N • HCl FW 261.79 H (R)-(+)-2‑Amino-1‑fluoro-4‑methyl- (S)-(−)-1,2,2‑Triphenylethylamine, 1,1‑diphenylpentane, 98% 97% 461520 [352535‑74‑1] [352535‑04‑7] CH − ‑ 3 NH2 NH2 ( )-Bis[(S)-1 phenylethyl]amine C18H22FN C20H19N H C hydrochloride, 97% FW 271.37 3 F FW 273.37

[40648‑92‑8] CH3 CH3 C16H19N · HCl N • HCl 554634 553220 FW 261.79 H ‑ ‑ (R)-(+)-1,2,2‑Triphenylethylamine, 445940 (S)-(+)-2 Amino-3,3 dimethyl- 1,1‑diphenylbutane, 99% 97% − ‑ ‑ ‑ (S)-( )-2 Amino-1 fluoro-3 methyl- ‑ ‑ C20H19N [352535 91 2] NH ‑ NH2 2 1,1 diphenylbutane, 97% C18H23N FW 273.37 t-Bu FW 253.38 C17H20FN NH2 FW 257.35 H3C F CH3 557919 553247

551074

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 33 (R)-(+)-1‑Benzyl-2,2‑diphenylethyl- (R)-N,N′-Dimethyl-1,1′-binaphthyl- Bis[(R)-(−)-(1‑naphthyl)ethyl]amine amine, 98% diamine, ≥99.0% hydrochloride, 98%

[94964‑58‑6] [93713‑30‑5] [312619‑39‑9] NH2 CH3 CH3 C21H21N C22H20N2 C24H23N · HCl NHCH3 N • HCl FW 287.40 FW 312.41 FW 361.91 H NHCH3

461652 554510 672408 Bis[(S)-(+)-(1‑naphthyl)ethyl]amine (S)-(−)-1‑Benzyl-2,2‑diphenylethyl- (S)-N,N′-Dimethyl-1,1′-binaphthyl- hydrochloride, 98% amine, 98% diamine, ≥99.0% [171867‑34‑8] CH3 CH3 [233772‑38‑8] [666175‑40‑2] C24H23N · HCl NH2 N • HCl H C21H21N C22H20N2 FW 361.91 NHCH FW 287.40 FW 312.41 3 NHCH3 461660 Organic Building Blocks

554529 672297

Amino Alcohols (R)-(−)-1‑Amino-2‑propanol, 98% (R)-(−)-2‑Amino-1‑butanol, 98% (R)-(−)-2‑Amino-3‑methyl-1‑butanol, 98% [2799‑16‑8] [5856‑63‑3] H3C H C OH NH2 3 ‑ ‑ C3H9NO C4H11NO NH2 [4276 09 9] OH CH3 FW 75.11 FW 89.14 C5H13NO H3C OH 238856 307084 FW 103.16 NH2

284483 (S)-(+)-1‑Amino-2‑propanol, 98% (S)-(+)-2‑Amino-1‑butanol, ≥98%

‑ ‑ ‑ ‑ ‑ ‑ ‑ [2799 17 9] H C [5856 62 2] (S)-(+)-2 Amino-3 methyl-1 buta- 3 H3C OH C H NO NH2 C H NO 3 9 OH 4 11 NH2 nol, 96% FW 75.11 FW 89.14 [2026‑48‑4] 238864 132527 CH3 C5H13NO H3C OH FW 103.16 (R)-(−)-2‑Amino-1‑propanol, 98% (1R,2R)-trans-2‑Aminocyclopenta- NH2 nol hydrochloride, 97% 186708 ‑ ‑ [35320 23 1] H C 3 OH C3H9NO [68327‑11‑7] NH2 OH (S)-(+)-1‑Dimethylamino-2‑pro- FW 75.11 C H NO · HCl 5 11 • HCl panol, 98% 297682 FW 137.61 NH2 [53636‑17‑2] 671878 OH CH3 (S)-(+)-2‑Amino-1‑propanol, 98% C5H13NO N H3C CH3 ‑ FW 103.16 ‑ ‑ (1S,2S)-trans-2 Aminocyclopenta- [2749 11 3] H C 3 OH nol hydrochloride, ≥98.0% (TLC) 462039 C3H9NO NH2 FW 75.11 ‑ ‑ [68327 04 8] OH (S)-(+)-2‑Amino-1‑pentanol, 97% A76206 C5H11NO · HCl • HCl NH2 ‑ ‑ FW 137.61 [22724 81 8] H C 3 OH (S)-3‑Amino-1,2‑propanediol, 98% C5H13NO 06782 NH2 FW 103.16 [61278‑21‑5] H2N OH ‑ 534587 C3H9NO2 OH (1R,2S)-cis-2 Aminocyclopentanol FW 91.11 hydrochloride, ≥98.0% (TLC) (R)-(−)-2‑Amino-1‑pentanol, 97% 473960 [137254‑03‑6] OH ‑ ‑ [80696 30 6] H C ‑ ‑ C5H11NO · HCl • HCl 3 OH (R)-3 Amino-1,2 propanediol, NH C5H13NO FW 137.61 2 NH2 ≥98.0% (T) FW 103.16 06756 534579 [66211‑46‑9] H2NOH C3H9NO2 OH FW 91.11 09267

34 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (1S,2S)-(+)-2‑Aminocyclohexanol (S)-(+)-Norepinephrine L-bitartrate, (1S,2S)-(+)-trans-1‑Amino-2‑indan- hydrochloride, 98.5‑101.5% (AT) 99% ol, 97%

[13374‑30‑6] [163061‑74‑3] OH OH OH O OH • HCl NH HO C H NO C6H13NO · HCl 2 • OH 9 11 NH2 FW 151.63 O OH FW 149.19 NH2 Blocks Building Organic HO 671959 OH 663344 [636‑88‑4] ‑ (1R,2R)-trans-2 Aminocyclohexanol C8H11NO3 ·C4H6O6 (R)-(−)-1‑Amino-6‑hydroxyindan, hydrochloride, 99% FW 319.26 97% 407453 ‑ ‑ [13374 31 7] OH C9H11NO C6H13NO · HCl • HCl Norepinephrine L-bitartrate hy- FW 149.19 FW 151.63 NH2 HO drate, 99% NH2 671762 675377 OH O OH OH (S)-(−)-(3‑Chloro-2‑hydroxypropyl) NH2 • HO (1R,2R)-(−)-2‑Amino-1-(4‑nitro- trimethylammonium chloride, 99% OH O HO • xH2O ‑ OH phenyl)-1,3 propanediol, 99% ‑ ‑ [101396 91 2] OH CH3 [339091‑66‑6] ‑ ‑ C H Cl NO Cl [716 61 0] OH 6 15 2 N CH3 Cl C8H11NO3 ·C4H6O6 ·xH2O C9H12N2O4 FW 188.10 CH3 OH FW 319.26 (Anh) FW 212.20 NH2 O2N 329177 392480 A70704 (S)-(+)-2‑Amino-1‑hexanol, 97% (S)-2-(Boc-amino)-1‑propanol, 98% (1S,2S)-(+)-2‑Amino-1-(4‑nitro- [80696‑29‑3] [79069‑13‑9] NH2 H3C ‑ OH phenyl)-1,3 propanediol, 99% C6H15NO H3C OH C8H17NO3 HN FW 117.19 FW 175.23 Boc ‑ ‑ [2964 48 9] OH 534560 469513 C9H12N2O4 OH

FW 212.20 NH2 O2N (R)-(−)-2‑Amino-1‑hexanol, 97% (1S,2R)-(−)-cis-1‑Amino-2‑indanol, 99% 471674 [80696‑28‑2] NH2 C6H15NO H3C OH [126456‑43‑7] (S)-(−)-2‑Amino-3‑phenyl-1‑pro- FW 117.19 NH2 C9H11NO panol, 98% 534552 FW 149.19 OH [3182‑95‑4] OH 440833 (S)-(−)-3-tert-Butylamino- C9H13NO NH2 1,2‑propanediol, 97% FW 151.21 (1R,2S)-(+)-cis-1‑Amino-2‑indanol, 190438 [30315‑46‑9] CH3 OH 99% C7H17NO2 H3C NH OH (R)-(+)-2‑Amino-3‑phenyl-1‑pro- CH3 ‑ ‑ FW 147.22 [136030 00 7] NH 2 panol, 98% C9H11NO 472980 OH FW 149.19 [5267‑64‑1] OH C H NO (R)-(−)-2‑Amino-1‑phenylethanol, 440841 9 13 NH2 97% FW 151.21 (1R,2R)-(−)-trans-1‑Amino-2‑indan- 284491 [2549‑14‑6] OH ol, 97% C8H11NO NH2 (1S,2S)-(+)-2‑Amino-1‑phenyl- FW 137.18 [163061‑73‑2] 1,3‑propanediol, 98% OH C9H11NO 494577 ‑ ‑ FW 149.19 NH2 [28143 91 1] OH C9H13NO2 ‑ ‑ 663336 OH (S)-2 Amino-1 phenylethanol, FW 167.21 NH2 ≥97.0% (GC, sum of enantiomers) 186546 ‑ ‑ [56613 81 1] OH C8H11NO NH2 FW 137.18

09222

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 35 (1R,2R)-(−)-2‑Amino-1‑phenyl- (1S,2S)-trans-N-Boc-2‑aminocyclo- (R)-(−)-2-tert-Butylamino-1‑phenyl- 1,3‑propanediol, 98% pentanol ethanol, 97%

‑ ‑ ‑ ‑ ‑ ‑ [46032 98 8] OH [145106 43 0] OH [14467 51 7] OH CH H 3 C9H13NO2 C10H19NO3 C12H19NO N CH3 OH Boc N CH3 FW 167.21 NH2 FW 201.26 H FW 193.29

248886 671436 551953

(S)-(+)-2‑Amino-3‑cyclohexyl-1‑pro- (1R,2R)-trans-N-Boc-2‑aminocyclo- (S)-(+)-2-tert-Butylamino-1‑phenyl- panol hydrochloride, 97% pentanol, ≥98.5% (GC) ethanol, 97%

‑ ‑ ‑ ‑ ‑ ‑ [117160 99 3] [454170 16 2] OH [14467 32 4] OH CH OH H 3 C9H19NO · HCl NH • HCl C10H19NO3 C12H19NO N CH3 2 Boc N CH3 FW 193.71 FW 201.26 H FW 193.29 432261 671312 551961 Organic Building Blocks N-Boc-(S)-(−)-2‑amino-1‑butanol, (S)-(−)-2-(Boc-amino)-1,5‑pentane- (S)-(+)-2‑Amino-2-(4-tert-butyl- 96% diol, 97% phenyl)ethanol, 97% [150736‑72‑4] H3C OH ‑ ‑ [162955 48 8] C12H19NO NH2 C9H19NO3 HN HO OH OH Boc C10H21NO4 HN FW 193.29 FW 189.25 Boc FW 219.28 H3C 660116 H3C 536644 CH3 N-Boc-(R)-(+)-2‑amino-1‑butanol, 666130 (1S,2S)-trans-N-Boc-2‑aminocyclo- 96% hexanol, 99% (1S,2R)-(+)-2‑Amino-1,2‑diphenyl- C9H19NO3 H3C OH ‑ ‑ ethanol, 99% [145166 06 9] OH FW 189.25 HN Boc C H NO 11 21 3 Boc ‑ ‑ N [23364 44 5] FW 215.29 H NH2 660108 C14H15NO

670987 FW 213.28 OH (S)-(−)-2-(Boc-amino)-1,4‑butanediol, 97% (1R,2R)-trans-N-Boc-2‑aminocyclo- 331880 hexanol, 99% ‑ ‑ [128427 10 1] HO (1R,2S)-(−)-2‑Amino-1,2‑diphenyl- C H NO OH ‑ ‑ 9 19 4 HN [155975 19 2] OH ethanol, 99% FW 205.25 Boc C11H21NO3 Boc N ‑ ‑ 536652 FW 215.29 H [23190 16 1] NH2 C14H15NO 670863 FW 213.28 (1S,2S)-(+)-2‑Amino-3‑methoxy- OH 1‑phenyl-1‑propanol, 98% N-Boc-(2S,3S)-(−)-2‑amino-3‑meth- 331899 ‑ [51594‑34‑4] yl-1 pentanol, 96% OH − ‑ ‑ C10H15NO2 (S,S)-( )-2 Amino-1,2 diphenyl- OCH3 ‑ ‑ [106946 74 1] Boc ≥ FW 181.23 NH2 NH ethanol, 99.5% (HPLC) C H NO 11 23 3 OH H C 316520 FW 217.31 3 [23190‑17‑2] CH3 NH2 C14H15NO 660205 (R)-(+)-2‑Amino-3‑benzyloxy-1‑pro- FW 213.28 OH panol, 97% (+)-2‑Amino-N-[(1S,2S)-(2‑hydroxy- 671223 [58577‑87‑0] ‑ ‑ O OH 1 methyl-2 phenyl)ethyl]-N- C10H15NO2 ‑ ‑ NH2 methylacetamide, 97% (R,R)-(+)-2 Amino-1,2 diphenyl- FW 181.23 ethanol, ≥99.5% (HPLC) 473758 [170115‑96‑5] ‑ ‑ C12H18N2O2 [88082 66 0] NH2 FW 222.28 C14H15NO (1S,2S)-(+)-Thiomicamine, 99% CH3 HO FW 213.28 N OH NH ‑ ‑ H3C 2 [16854 32 3] OH O 671126 C10H15NO2S OH

FW 213.30 NH2 516120 H3CS

361887

36 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (1R,2R)-(−)-N-Boc-2‑amino-1- (R)-(−)-2‑Benzylamino-1‑phenyl- (S)-(−)-2‑Amino-4‑methyl-1,1‑di- (4‑nitrophenyl)-1,3‑propanediol, ethanol, 97% phenyl-1‑pentanol, 98% 96% [107171‑75‑5] [78603‑97‑1] CH3 NH OH H 2 ‑ ‑ C15H17NO N C18H23NO [366487 74 3] OH H C 3 OH C H N O FW 227.30 FW 269.38 Blocks Building Organic 14 20 2 6 OH FW 312.32 HN O N 2 Boc 551988 660213 554561 (S)-(+)-2‑Benzylamino-1‑phenyl- cis-(1S,2R)-(−)-2-(Benzylamino) ethanol, 97% (S)-(−)-2‑Amino-3,3‑dimethyl- cyclohexanemethanol, 99% 1,1‑diphenyl-1‑butanol, 99% [51096‑49‑2] OH H [71581‑93‑6] C15H17NO N [144054‑70‑6] OH FW 227.30 NH2 C14H21NO C18H23NO N t-Bu FW 219.32 H FW 269.38 OH 551996

405086 ‑ (R)-(+)-3 Benzyloxy-2-(Boc-amino)- 557900 ‑ (1S,2S)-(+)-N-Boc-2‑amino-1‑phe- 1 propanol, 98% ‑ − ‑ nyl-1,3 propanediol, 97% [127559‑33‑5] (2R,3S)-( )-4 Dimethylamino- O OH 1,2‑diphenyl-3‑methyl-2‑butanol, C15H23NO4 HN C14H21NO4 Boc Boc NH FW 281.35 99% FW 267.32 HO 473766 [72541‑03‑8] OH CH3 CH3 C19H25NO N ‑ ‑ ‑ CH3 661066 (R)-(+)-2 Amino-3 methyl-1,1 di- FW 283.41 Ph OH phenyl-1‑butanol, 98% (R)-(+)-Atenolol, 99% 517844 [86695‑06‑9] NH2 ® C17H21NO H3C NH2 Chirald , 99% CH3 FW 255.35 OH O CH3 H3C N O H [38345‑66‑3] OH CH3 CH3 C19H25NO N ‑ ‑ CH3 [56715 13 0] 551082 FW 283.41 HO Ph C14H22N2O3 FW 266.34 227404 (S)-(−)-2‑Amino-3‑methyl-1,1‑di- 330884 phenyl-1‑butanol, 98% (S)-2-(N,N-Dibenzylamino)- (S)-(−)-2-(Boc-amino)-3‑cyclohexyl- [78603‑95‑9] 3‑methylbutanol, 90% NH2 1‑propanol, 90% C17H21NO H3C OH [111060‑54‑9] FW 255.35 CH3 [103322‑56‑1] C19H25NO N OH H3C OH C14H27NO3 HN FW 283.41 Boc CH FW 257.37 551015 3 421693 538167 (S)-(+)-2-(Dibenzylamino)-1‑pro- (R)-(+)-2‑Amino-1,1‑diphenyl- panol, 99% (S)-(−)-2‑Amino-1,1,2‑triphenyl- 1‑propanol, 99% ethanol, 97% [60479‑65‑4] ‑ ‑ N [78603 93 7] C17H21NO ‑ ‑ NH2 [129704 13 8] H C NH2 C15H17NO FW 255.35 3 CH3 OH C20H19NO FW 227.30 HO FW 289.37 OH 349607

549460 (R)-(+)-2‑Amino-4‑methyl-1,1‑di- 553255 phenyl-1‑pentanol, 98% (S)-(−)-2‑Amino-1,1‑diphenyl-1‑pro- (S)-(+)-2-(N,N-Dibenzylamino)- [161832‑74‑2] panol, 99% CH 3 NH2 4‑methylpentanol, 90% C18H23NO H C ‑ ‑ 3 OH [78603 91 5] FW 269.38 [111060‑53‑8] NH2 N C15H17NO CH3 C20H27NO FW 227.30 HO FW 297.43 OH H C 554553 3 CH3

549479 538183

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 37 (R)-(+)-2‑Amino-1,1,3‑triphenyl- (R)-(+)-N-Carbomethoxy-2‑amino- (S)-(+)-2-(Dibenzylamino)-3‑phe- 1‑propanol, 98% 1,1,2‑triphenylethanol, 98% nyl-1‑propanol, 99%

‑ ‑ ‑ ‑ ‑ ‑ [86906 05 0] [352535 67 2] O OCH [111060 52 7] NH2 3 N C21H21NO C22H21NO3 NH C23H25NO OH FW 303.40 FW 347.41 OH FW 331.45 OH

554472 554413 421731

(S)-(−)-2‑Amino-1,1,3‑triphenyl- (S)-(−)-N-Carboxymethoxy-2‑ami- 1‑propanol, 98% no-1,1,2‑triphenylethanol, 99%

[79868‑78‑3] NH2 C22H21NO3 O OCH3 C21H21NO FW 347.41 NH OH FW 303.40 OH Organic Building Blocks

554464 554421

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38 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Aziridines

Lithium L-aziridine-2‑carboxylate, (S)-1-[(R)-α-Methylbenzyl]aziri- (−)-Menthyl (R)-1-[(R)-α-methyl- ≥97.0% (NT, dried material) dine-2‑methanol, 98% benzyl]aziridine-2‑carboxylate, 98% [67413‑27‑8] [173143‑73‑2] Blocks Building Organic O OH C H LiNO C H NO 3 4 2 O– 11 15 N C21H31NO2 CH3 FW 93.01 N Li+ FW 177.24 H3C Ph FW 329.48 H O

O 11558 570532 N H3C CH3

H3C (S)-1-[(R)-α-Methylbenzyl)aziri- 1‑Benzyl 2‑methyl (S)-(−)-1,2‑aziridine-2‑carboxamide, 98% dinedicarboxylate, 96% 570540 ‑ ‑ [104597‑98‑0] [75985 51 2] O O C12H13NO4 − α C11H14N2O NH OCH3 ( )-Menthyl (S)-1-[(R)- -methyl- 2 N FW 190.24 N FW 235.24 ‑ Cbz benzyl]aziridine-2 carboxylate, H3C Ph 98% 516031 570524 C21H31NO2 CH3 (S)-(+)-2‑Benzyl-1-(p-tolylsulfonyl) FW 329.48 α O (R)-1-[(1R)- -Methylbenzyl]aziri- aziridine, 98% ‑ O dine-2 carboxamide, 98% N [62596‑64‑9] H3C CH3 [75985‑52‑3] H3C O C16H17NO2S N C11H14N2O O S O NH2 FW 287.38 FW 190.24 N 570516

H3C CH3 Methyl (S)-(−)-1‑tritylaziridine- 570559 464015 2‑carboxylate, 98%

[75154‑68‑6] (R)-1-[(R)-α-Methylbenzyl)aziri- O C23H21NO2 dine-2‑methanol, 98% OCH3 FW 343.42 N [173034‑70‑3] OH C11H15NO N

FW 177.24 H3C Ph 516015 570567

Carboxylic Acids

(S)-(−)-Trifluorolactic acid, 98% (S)-(−)-2‑Chloropropionic acid, 99% Sodium L-lactate, ≥99.0% (NT) ‑ ‑ ‑ ‑ ‑ ‑ [125995 00 8] O [29617 66 1] O [867 56 1] O

C H F O F3C C H ClO H3C C H NaO H3C 3 3 3 3 OH 3 5 2 OH 3 5 3 ONa FW 144.05 OH FW 108.52 Cl FW 112.06 OH

532509 306797 71718

(R)-(+)-2‑Bromopropionic acid, (R)-(+)-2‑Chloropropionic acid, 99% L-(−)-Glyceric acid hemicalcium salt ≥ ≥ 98.0% (GC, sum of enantiomers) ‑ ‑ monohydrate, 97% (KT) [7474 05 7] O ‑ ‑ C3H5ClO2 H3C ‑ ‑ [10009 70 8] O OH [6057 35 8] O O H C FW 108.52 Cl C3H5BrO2 3 OH C3H5O4 · 0.5Ca · H2O HO H Ca2 • 2H O Br 2 FW 152.97 306800 FW 143.12 OH 18165 2 Sodium D-lactate, ≥99.0% (NT) 372412 (S)-(−)-2‑Bromopropionic acid, 99% ‑ ‑ [920 49 0] O ‑ ‑ H C [32644 15 8] O C3H5NaO3 3 ONa H C FW 112.06 OH C3H5BrO2 3 OH FW 152.97 Br 71716 385514

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 39 L-(+)-2‑Amino-3‑phosphonopro- L-(−)-Malic acid, 97% (S)-3‑Hydroxybutyric acid, pionic acid ≥97.0% (T) ‑ ‑ [97 67 6] O ‑ ‑ C H O HO ‑ ‑ [23052 80 4] O O 4 6 5 OH [6168 83 8] OH O HO P FW 134.09 O OH C H O C3H8NO5P OH 4 8 3 H C OH OH 3 FW 169.07 NH FW 104.10 2 112577 54925 A154 D-(+)-Malic acid, ≥97.0% (HPLC, (S)-(+)-4‑Amino-3‑hydroxybutyric Potassium L-tartrate, 97% sum of enantiomers) acid, 97% ‑ ‑ [921‑53‑9] [636 61 3] O O OH [7013‑05‑0] C H K O ·HO OK • H O C4H6O5 HO OH O 4 4 2 6 2 KO 2 OH C4H9NO3 H2N FW 244.28 OH O FW 134.09 O OH OH FW 119.12 02300 289949 542946

Organic Building Blocks − L-(−)-Malic acid disodium salt, D-( )-Tartaric acid, 99% (S)-(−)-4‑Amino-2‑hydroxybutyric ‑ 95 100% (enzymatic) ‑ ‑ acid, 96% [147 71 7] OH O C H O HO [138‑09‑0] 4 6 6 OH ‑ ‑ O [40371 51 5] O FW 150.09 O OH C4H4Na2O5 NaO H N ONa C4H9NO3 2 OH FW 178.05 O OH 483796 FW 119.12 OH

M9138 467359 L-(+)-Tartaric acid, 99% L-Malic acid disodium salt mono- ‑ ‑ (S)-(−)-2‑Formamidosuccinic anhy- [87 69 4] OH O hydrate, 98% HO C4H6O6 OH dride, 90% FW 150.09 O OH ‑ ‑ ‑ ‑ [207511 06 6] O OH [33605 73 1] H N H ONa • H2O T109 C4H4Na2O5 ·H2O NaO C5H5NO4 O O FW 196.07 O FW 143.10 O O (R)-(−)-3‑Hydroxybutyric acid 233935 421588 sodium salt Potassium L-tartrate monobasic, ‑ ‑ (R)-(+)-Methylsuccinic acid, 99% [13613 65 5] OH O 99% C4H7NaO3 H3C ONa [3641‑51‑8] FW 126.09 O CH3 ‑ ‑ OH [868 14 4] OH O C5H8O4 298360 HO HO FW 132.11 O C4H5KO6 OK FW 188.18 O OH Sodium (S)-3‑hydroxybutyrate, 415596 243531 ~97% (S)-(−)-Methylsuccinic acid, 99% ‑ ‑ Potassium D-tartrate monobasic [127604 16 4] OH O [2174‑58‑5] C4H7NaO3 O CH3 H3C ONa [57341‑16‑9] C H O OH O OH FW 126.09 5 8 4 HO C4H5KO6 O FW 132.11 O K+ -O H3145 FW 188.18 OH OH 415618 T2032 (S)-(+)-2‑Amino-4‑bromobutyric acid hydrobromide, 97% (S)-(−)-2‑Acetoxypropionic acid, L-(−)-Malic acid sodium salt, 95% [15159‑65‑6] 95‑100% (enzymatic) O C4H8BrNO2 · HBr Br ‑ ‑ OH • HBr [6034 46 4] O ‑ ‑ FW 262.93 NH2 C5H8O4 H3C O [68303 40 2] O OH C H NaO HO FW 132.11 O CH3 4 5 5 ONa 476986 FW 156.07 O OH 453382 M1125 (R)-3‑Hydroxybutyric acid, ≥98.0% (T) (R)-(−)-Citramalic acid, 98% Sodium hydrogentartrate, 98% [625‑72‑9] [6236‑10‑8] OH O O HO CH3 ‑ ‑ C4H8O3 C5H8O5 OH [526 94 3] OH O H3C OH HO C H NaO HO FW 104.10 FW 148.11 O 4 5 6 ONa FW 172.07 O OH 54920 329142 289981

40 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (R)-(+)-2‑Bromo-3‑methylbutyric (S)-(−)-2-(Trifluoroacetamido)suc- (S)-(−)-2‑Hydroxyisocaproic acid, acid, 96% cinic anhydride, 97% 98%

[76792‑22‑8] [777‑33‑3] [13748‑90‑8] CH3 O O CF3 CH3 OH C5H9BrO2 C6H4F3NO4 C6H12O3 OH H3C OH NH H3C

FW 181.03 Br FW 211.10 FW 132.16 O Blocks Building Organic O O O 468347 219827 305251 (S)-(−)-2‑Bromo-3‑methylbutyric (S)-(+)-2,2‑Dimethyl-5‑oxo-1,3‑di- − ‑ acid, 96% (S)-( )-2 Acetoxysuccinic anhy- oxolane-4‑acetic acid, 95% dride, 98% ‑ ‑ [26782 75 2] CH O [73991‑95‑4] 3 ‑ ‑ O OH C H BrO [59025 03 5] CH 5 9 2 H C OH O 3 C7H10O5 3 OOO FW 181.03 Br C6H6O5 O FW 174.15 O O FW 158.11 O H3C CH3 462101 422800 445584 (S)-2‑Chloro-3‑methylbutyric acid, ‑ − ‑ ‑ ‑ ≥90% (GC) (R)-(+)-2 Acetoxysuccinic anhy- (R)-( )-2,2 Dimethyl-5 oxo-1,3 di- dride, 96% oxolane-4‑acetic acid, 95% ‑ ‑ [26782 74 1] CH O 3 [79814‑40‑7] [113278‑68‑5] C5H9ClO2 O CH3 O H3C OH OH Cl C6H6O5 C7H10O5 FW 136.58 O OOO FW 158.11 O O O FW 174.15 25113 H3C CH3 441570 460028 (R)-2‑Chloro-3‑methylbutyric acid, (+)-Potassium D -threo-isocitrate ≥90% (GC) s − ‑ monobasic, ≥98.0% (NT) (R)-( )-2 Chloromandelic acid, 99% ‑ ‑ [84918 96 7] CH O ‑ ‑ 3 ‑ ‑ [52950 18 2] Cl OH [20226 99 7] OK C5H9ClO2 O H3C OH O O C8H7ClO3 OH C6H7KO7 FW 136.58 Cl FW 230.21 HO OH FW 186.59 O OH 25112 478873 58790 (S)-(+)-2‑Methylbutyric acid, 98% (S)-(+)-2‑Chloromandelic acid, 97% Calcium L-lactate hydrate, ≥98.0% ‑ ‑ [1730 91 2] O ‑ ‑ (KT, calc. based on dry substance) [52950 19 3] OH C5H10O2 H C OH 3 C8H7ClO3 OH FW 102.13 CH3 [41372‑22‑9] O FW 186.59 O Cl C6H10CaO6 ·xH2O H3C 245526 O Ca2+ • xH2O FW 218.22 (Anh) OH 562823 2 (S)-(+)-2‑Hydroxy-3‑methylbutyric − ‑ acid, 99% 21185 (R)-( )-3 Chloromandelic acid, 97% [61008‑98‑8] [17407‑55‑5] L OH CH3 O Magnesium -lactate hydrate, C8H7ClO3 OH C5H10O3 H C OH ≥95.0% (KT, calc. based on dry 3 FW 186.59 O FW 118.13 OH substance) Cl 379093 [18917‑93‑6] O 445444

C6H10MgO6 ·xH2O HO 2+ α O Mg • xH2O D- -Hydroxyisovaleric acid, FW 202.45 (Anh) CH3 − ≥ ≥98.0% (T) 2 (R)-( )-Mandelic acid, 99% 63097 ‑ ‑ [17407‑56‑6] [611 71 2] OH CH3 O C8H8O3 OH C5H10O3 H C OH 3 (S)-(−)-2‑Hydroxy-3,3‑dimethyl- FW 152.15 O FW 118.13 OH butyric acid, 97% 55452 154210 ‑ ‑ [21641 92 9] O t-Bu ≥ C6H12O3 OH (S)-(+)-Mandelic acid, 99% FW 132.16 OH ‑ ‑ [17199 29 0] OH 410918 C8H8O3 OH FW 152.15 O

M2004

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 41 (+)-O,O′-Diacetyl-L-tartaric anhy- (R)-(−)-α-Methoxyphenylacetic (S)-(−)-α-Methoxy-α-(trifluoro- dride, 97% acid, 99% methyl)phenylacetic acid, ≥99%

[6283‑74‑5] [3966‑32‑3] [17257‑71‑5] O O OCH3 H3CO CF3 O O OH C8H8O7 C9H10O3 OH C10H9F3O3 H3C CH3 FW 216.14 FW 166.17 O FW 234.17 O O O O

358924 248967 318035 α α (R)-(−)-Hexahydromandelic acid, (S)-(+)-α-Methoxyphenylacetic acid (R)-(+)- -Methoxy- -trifluoro- 98% methylphenylacetic acid, 99% [26164‑26‑1] OCH3 ‑ ‑ ‑ ‑ C9H10O3 OH [20445 31 2] CF [53585 93 6] OH H3CO 3 FW 166.17 O C10H9F3O3 OH C8H14O3 OH FW 158.19 O FW 234.17 O 248983 301140 155268 Organic Building Blocks (S)-3‑Hydroxy-3‑phenylpropionic (S)-(+)-Hexahydromandelic acid, acid, ≥98.0% (GC, sum of enan- (S)-(−)-α-Methoxy-α-(trifluoro- 98% tiomers) methyl)phenylacetic acid, 98% ‑ ‑ ‑ ‑ [17257‑71‑5] [61475 31 8] OH [36567 72 3] OH O H3CO CF3 OH OH C H O C10H9F3O3 C8H14O3 9 10 3 OH FW 158.19 O FW 166.17 FW 234.17 O

301159 56193 155616

(S)-2‑Bromo-3‑phenylpropionic (R)-(+)-2-(4‑Hydroxyphenoxy)pro- (R)-(–)-α-Acetylmandelic acid, 99% ≥ acid, 95.0% (T) pionic acid, 98% ‑ ‑ [51019 43 3] O

‑ ‑ ‑ ‑ C10H10O4 H C O [35016 63 8] O [94050 90 5] O 3 FW 194.18 OH C H O O C9H9BrO2 OH 9 10 4 OH O FW 229.07 FW 182.17 CH Br HO 3 253030 00031 474533 (S)-(+)-O-Acetylmandelic acid, 99% (S)-(+)-2‑Phenylpropionic acid, 97% (1S,2R)-1‑Methyl cis-1,2,3,6‑tetra- hydrophthalate, 97% ‑ ‑ [7782‑24‑3] [7322 88 5] O CH3 C10H10O4 C9H10O2 OH [88335‑93‑7] H3C O O FW 194.18 OH FW 150.17 O C9H12O4 OCH3 O FW 184.19 OH 279900 O 253022 (R)-(−)-2‑Phenylpropionic acid, 367281 − ≥ 97% (R)-( )-Phenylsuccinic acid, 96.0% [1S-(1β,2α,3β)]-(+)-3‑Methyl-2- (HPLC, sum of enantiomers) [7782‑26‑5] CH3 ‑ (nitromethyl)-5 oxocyclopentane- [46292‑93‑7] C9H10O2 OH O acetic acid, 98% C10H10O4 HO FW 150.17 O OH FW 194.18 [123000‑45‑3] O 279897 O C9H13NO5 OH FW 215.20 − ‑ O 78172 L-( )-3 Phenyllactic acid, 98% NO2

‑ ‑ CH3 [20312 36 1] O (S)-(+)-Phenylsuccinic acid, ≥99.0% C H O 647497 9 10 3 OH (HPLC, sum of enantiomers) FW 166.17 OH Aluminum L-lactate, 98‑102% (re- [4036‑30‑0] 113069 O C10H10O4 HO lated on reference to anhydrous OH substance) FW 194.18 O D-(+)-3‑Phenyllactic acid, 98% [18917‑91‑4] ‑ ‑ O [7326 19 4] O C9H15AlO9 H C 78173 3 O- Al3+ C9H10O3 OH FW 294.19 OH 3 FW 166.17 OH 25301 376906

42 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-(−)-2-(Phenylcarbamoyloxy)pro- (S)-2‑Hydroxy-2‑phenylbutyric (1R,3S)-(+)-Camphoric acid, 99% pionic acid, 98% acid, 96% ‑ ‑ [124 83 4] O ‑ ‑ ‑ ‑ C10H16O4 [102936 05 0] O [24256 91 5] O OH H CH3 C10H11NO4 N O C10H12O3 FW 200.23 HO OH H3C OH CH3 OH H3C Ph O Blocks Building Organic FW 209.20 O CH3 FW 180.20 676691 328243 C409 ‑ ‑ − (R)-(−)-2‑Phenylbutyric acid, 99% (R)-2 Hydroxy-4 phenylbutyric (1S,3R)-( )-Camphoric acid, 99% acid, 99% ‑ ‑ [938‑79‑4] [560 09 8] O O ‑ ‑ [29678 81 7] C10H16O4 OH C10H12O2 H C OH O 3 CH3 C10H12O3 FW 200.23 HO FW 164.20 CH OH H3C 3 FW 180.20 OH O 376345 279870 420085 ′ (R)-(+)-Citronellic acid, 98% (S)-(+)-2‑Phenylbutyric acid, 99% (S,S)-Ethylenediamine-N,N -di- succinic acid trisodium salt solution [18951‑85‑4] [4286‑15‑1] CH3 CH3 O O C H O ‑ ‑ 10 18 2 H C OH C10H12O2 [178949 82 1] O OH 3 H3C OH O FW 170.25 C H N Na O H FW 164.20 10 13 2 3 8 N N O- 340499 FW 358.19 H O + O O- Na Na+ - Na+ 279889 O (S)-(−)-Citronellic acid, 98% 92698 [2111‑53‑7] (R)-3‑Phenylbutyric acid, ≥98.5% CH3 CH3 O C10H18O2 (GC, sum of enantiomers) − H3C OH (S)-( )-Perillic acid, 95% FW 170.25 [772‑14‑5] ‑ ‑ 364428 CH3 O [23635 14 5] O C10H12O2 C H O OH 10 14 2 OH FW 164.20 ‑ FW 166.22 H2C (S)-(+)-2 Methylbutyric anhydride, CH 94% 78239 3 ‑ ‑ 218359 [84131 91 9] O O (S)-3‑Phenylbutyric acid, ≥99.0% C10H18O3 H3C O CH3 (HPLC, sum of enantiomers) (1S)-(+)-Ketopinic acid, 99% FW 186.25 CH3 CH3

‑ ‑ 348562 [772 15 6] CH O [40724‑67‑2] 3 CH3 H3C C10H12O2 OH C10H14O3 FW 164.20 FW 182.22 (R)-3-(Boc-amino)-5-hexynoic 8 HO O acid, 98% 78240 O ‑ ‑ [332064 91 2] Boc 420964 NH O (R)-(+)-2-(Benzyloxy)propionic acid, C11H17NO4 FW 227.26 HC OH ≥97.0% (HPLC) (1S)-(−)-Camphanic acid, 99% 711942 ‑ ‑ [100836 85 9] [13429‑83‑9] O H3C CH3 C10H12O3 O 8 OH C10H14O4 CH3 (S)-3-(Boc-amino)-5-hexynoic FW 180.20 O CH3 FW 198.22 O acid, 98% O OH ‑ ‑ 00696 [270596 47 9] Boc NH O 328227 C11H17NO4 HC OH (R)-2‑Hydroxy-2‑phenylbutyric FW 227.26 acid, 96% (+)-trans-Chrysanthemic acid, 711934 ≥98.0% (GC) ‑ ‑ 8 [3966 31 2] O (R)-3-(Boc-amino)-5-hexenoic C10H12O3 [4638‑92‑0] H3C OH O acid, 98% Ph OH FW 180.20 C10H16O2 H3C OH ‑ ‑ FW 168.23 [269726 94 5] Boc 676705 H3C NH O H3C CH3 C11H19NO4 FW 229.27 H2C OH 18509 711969

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 43 (S)-3-(Boc-amino)-5-hexenoic 8 (+)-Menthyloxyacetic acid, 98% (R)-(−)-6‑Methoxy-α-methyl- acid, 98% 2‑naphthaleneacetic acid, 98% ‑ ‑ [94133 41 2] O [270263‑03‑1] Boc C12H22O3 H3C O [23979‑41‑1] NH O OH CH3 C11H19NO4 FW 214.30 CH3 C14H14O3 OH FW 229.27 H2C OH CH3 FW 230.26 O H3CO 711950 448397 570842 (R)-(+)-N-(1‑Phenylethyl)succinamic (R)-α-Methoxy-2‑naphthylacetic acid, 98% Naproxen, 98% acid, ≥99.0% ‑ ‑ [21752‑33‑0] [22204 53 1] CH CH3 O [156942‑67‑5] 3 OH OCH3 C14H14O3 OH C12H15NO3 N H C13H12O3 OH FW 221.25 O FW 230.26 O H3CO FW 216.23 O 461423 284785 669865 Organic Building Blocks (S)-(−)-N-(1‑Phenylethyl)succinamic − α ‑ ‑ (S)-α-Methoxy-2‑naphthylacetic (R)-( )- -[(3 Ethoxy-1 methyl- acid, 98% ‑ ‑ acid, 97% 3 oxo-1 propenyl)amino]benzene- acetic acid potassium salt, 97% [21752‑34‑1] CH3 O ‑ ‑ [157134 51 5] OCH C12H15NO3 OH 3 ‑ ‑ N [961 69 3] CH O H C13H12O3 OH 3 FW 221.25 O C14H16KNO4 FW 216.23 O HN O CH3 FW 301.38 OK 461431 669989 O

(S)-(+)-Z-4‑Amino-2‑hydroxybutyric 471666 (R)-(+)-α-[(3‑Methoxy-1‑methyl- acid, 97% 3‑oxo-1‑propenyl)amino]-1,4‑cyclo- (1R,2S)-(−)-2‑Benzamidocyclo- ‑ ‑ ‑ [40371 50 4] O hexadiene-1 acetic acid sodium H hexanecarboxylic acid, 97% C H NO N 12 15 5 Cbz OH salt, 98% FW 253.25 OH [26693‑55‑0] [26774‑89‑0] HO O O C H NO H 533106 14 17 3 N C13H16NNaO4 ONa FW 247.29 FW 273.26 O H3CO NH (R)-(+)-3‑Hydroxy-5‑oxo-1‑cyclo- O CH3 pentene-1‑heptanoic acid, 96% 568090 471631 ‑ ‑ [54996 33 7] O O (1S,2R)-(+)-2‑Benzamidocyclo- C H O 12 18 4 OH (S)-(+)-Ibuprofen, 99% hexanecarboxylic acid, 97% FW 226.27 HO [51146‑56‑6] [26685‑82‑5] CH3 HO O H 473057 C13H18O2 OH C14H17NO3 CH3 N FW 206.28 O FW 247.29 H3C O [1R-(2-endo,3-exo)]-3‑Hydroxy- 4,7,7‑trimethylbicyclo[2.2.1]hep- 375160 568104 tane-2‑acetic acid, 99% (S)-2-(Boc-amino)octanedioic acid, (+)-O,O′-Di-pivaloyl-D-tartaric acid, [81925‑04‑4] 97% CH3 ≥98.0% (T) H C C12H20O3 3 O H [66713‑87‑9] FW 212.29 OH O [76769‑55‑6] OH O H C C H NO HO 3 H 13 23 6 OH C H O 14 22 8 O O t-Bu FW 289.32 O HN Boc FW 318.32 OH 309664 HO t-Bu O O 671983 (−)-Menthyloxyacetic acid, 98% O (R)-2-(Boc-amino)octanedioic acid, 43456 [40248‑63‑3] O 99% H C O C12H22O3 3 OH FW 214.30 CH ‑ ‑ 3 [75113 71 2] O CH HO 3 C13H23NO6 OH FW 289.32 O HN M3000 Boc 672092

44 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (−)-O,O′-Di-pivaloyl-L-tartaric acid, (S)-(−)-N-(1‑Phenylethyl)phthal- Rosmarinic acid, 97% ≥98.0% (T) amic acid, 97% ‑ ‑ [20283 92 5] HO ‑ ‑ ‑ ‑ C H O O [65259 81 6] O [21752 36 3] O 18 16 8 O FW 360.31 HO OH C14H22O8 O O t-Bu C16H15NO3 OH O OH

FW 318.32 OH FW 269.30 NH Blocks Building Organic HO OH t-Bu O O O CH3 O 536954 461466 43457 (−)-mono-(1R)-Menthyl phthalate, (S)-(−)-N-[1-(1‑Naphthyl)ethyl]suc- 99% (R)-(−)-2‑Fluoro-α-methyl- cinamic acid, 98% ‑ 4 biphenylacetic acid, 97% [33744‑74‑0] [212556‑04‑2] CH3 O OOH ‑ ‑ C18H24O4 O [51543 40 9] F C16H17NO3 HO O NH CH3 FW 304.38 C15H13FO2 FW 271.31 O O OH FW 244.26 H3CCH3 CH3

545740 448443 461644 ‑ α Ricinoleic acid, ~80% (GC) (S)-(+)-2 Fluoro- -methyl- (R)-(+)-N-[1-(1‑Naphthyl)ethyl]suc- ‑ 4 biphenylacetic acid, 98% [141‑22‑0] cinamic acid, 98% O C18H34O3 [51543‑39‑6] OH F O ‑ ‑ [78681 09 1] O FW 298.46 HO C15H13FO2 OH C16H17NO3 HO FW 244.26 NH CH3 (CH2)5CH3 CH3 FW 271.31 O 83903 482641

(R)-2-[(Boc-amino)methyl]-3- 8 461636 L-Lactic acid tetrabutylammonium phenylpropionic acid, 97% salt solution (+)-2,3‑Dibenzoyl-D-tartaric acid, ‑ ‑ [262301 38 2] ≥ O O 98% H3C CH3 Boc N H3C C15H21NO4 N OH O H H C CH3 ‑ ‑ 3 OH FW 279.33 [17026 42 5] O C18H14O8 Ph O O C19H41NO3 FW 358.30 HO FW 331.53 698660 OH O O Ph 69784 O (S)-2-[(Boc-amino)methyl]-3- 8 ‑ phenylpropionic acid, 97% 163449 (S)-(+)-N-[1-(1 Naphthyl)ethyl] phthalamic acid, 98% [189619‑55‑4] O Dibenzoyl-L-tartaric acid, 98% Boc [163438‑06‑0] C15H21NO4 N OH O H FW 279.33 ‑ ‑ C20H17NO3 [2743 38 6] HO O OH O FW 319.35 NH CH3 C18H14O8 O FW 358.30 O O O 697680 O OH

345849 (S)-(+)-Ketoprofen, 99% 399736

[22161‑81‑5] (−)-O,O′-Dibenzoyl-L-tartaric acid O CH3 (R)-(−)-N-[1-(1‑Naphthyl)ethyl] ≥ C16H14O3 OH monohydrate, 99.0% (T) phthalamic acid, 98% FW 254.28 O O ‑ ‑ [163438 05 9] O 471909 HO O C20H17NO3 OH O • H2O FW 319.35 NH CH3 (R)-(+)-N-(1‑Phenylethyl)phthal- O O O HO O amic acid, 97% [62708‑56‑9] [21752‑35‑2] C18H14O8 ·H2O O 399728 C H NO FW 376.31 16 15 3 OH FW 269.30 NH 33622

O CH3

461458

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 45 (+)-O,O′-Di-p-toluoyl-D-tartaric Di-p-toluoyl-D-tartaric acid mono- N,N-Bis[(S)-(−)-1‑phenylethyl] acid, 97% hydrate, 98% phthalamic acid, 98%

H C HO O H3C HO O C24H23NO3 3 O O • H2O CH O O FW 373.44 3 O O N O O O O O OH CH3 O OH CH3 H3C [32634‑68‑7] [71607‑31‑3] OH

C20H18O8 C20H18O8 ·H2O FW 386.35 FW 404.37 461687 302813 108081

(−)-O,O′-Di-p-toluoyl-L-tartaric acid, N,N-Bis[(R)-(+)-1‑phenylethyl] 97% phthalamic acid, 98%

‑ ‑ O OH [312619 40 2] H3C

Organic Building Blocks O C24H23NO3 CH O 3 O FW 373.44 N O O O O OH CH3 H3C OH [32634‑66‑5]

C20H18O8 FW 386.35 461679 371416

46 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (R)-(+)- and (S)-(–)-Stericol®: New, Effective Chiral Auxiliaries

The introduction of chirality to organic molecules through 1-(2,4,6-triisopropyl)phenylethanol ((R)- and (S)-Stericol®) the use of auxiliaries is a basic strategy in organic are especially beneficial as chiral auxiliaries, providing high chemistry. Chiral benzylic alcohols are of particular interest diasteromeric ratios in [2+2] cycloadditions,1 oxidations,2 because they often afford useful levels of stereoselection and carbon-carbon bond forming reactions.3 and are generally easy to cleave. The enantiomers of

Preparation of Dichlorocyclobutanones i-Pr OH

CH3 i-Pr Cl CH3 i-Pr i-Pr i-Pr 1) KH, Cl2C=CHCl CH3 C O R OH n-BuLi, RI O Cl (R)-(+)-1-(2,4,6-Triisopropylphenyl)ethanol 2) LiAlH C H O i-Pr i-Pr 4 i-Pr i-Pr 17 28 248.40 [181531-14-6] Cl O Lactones 672599 Cl H3C Cyclopentanones Amino Acids O R Ar Alkaloids i-Pr OH up to 19:1 dr CH3 Ar = 2,4,6-(i-Pr) C H 3 6 2 i-Pr i-Pr (S)-(–)-1-(2,4,6-Triisopropylphenyl)ethanol

C17H28O Asymmetric Oxidation of Benzenesulfenates 248.40 [102225-88-7] 672483 O O i-Pr P(Oi-Pr) i-Pr O P(Oi-Pr) CH3 2 Cl S O CH3 2 Cl O N S O S References: (1) (a) de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1995, 60, 4940. (b) O O * CCl , rt Kanazawa, A. et al. J. Chem. Soc. Perkin Trans. 1997,1911. (c) Nebois, P.; Greene, A. E. J. Org. i-Pr i-Pr 4 i-Pr i-Pr Chem. 1996, 61, 5210. (d) Ceccon, J. et al. Synlett 2005, 1413. (e) Roche, C. et al. Org. Lett. 2003, 5, 1741. (f) Muniz, M. N. et al. Synlett 2005, 1328. (g) Roche, C. et al. J. Org. Chem. 2005, up to 13:1 dr 70, 8352. (h) Ceccon, J. et al. Org. Lett. 2006, 8, 4739. (2) Hamel, M.; Grach, G.; Abrunhosa, I.; Gulea, M.; Masson, S.; Vazeux, M.; Drabowicz, J.; Mikolajczyk, M. Tetrahedron: Asymmetry 2005, 16, 3406. (3) (a) Narkevitch, V. et al. Angew. Chem., Int. Ed. 2000, 39, 1806. (b) Bouchez, L. C. et al. Tetrahedron 2005, 61, 11473. (c) Narkevitch, V. et al. J. Org. Chem. 2001, 66, 5080. Preparation of β,γ-Unsaturated Silyl Sulfinates

i-Pr

i-Pr i-Pr CH3 OTMS O Yb(OTf)3, SO2 i-Pr CH + 3 CH R CH SO2TMS i-Pr i-Pr 3 2 CH2Cl2, -90 °C O O R

CH3 up to 25:1 dr

sigma-aldrich.com

misc.indd 2 6/18/2009 8:24:09 AM Cyanides/Nitriles (R)-(+)-4‑Chloro-3‑hydroxybutyro- (R)-2‑Acetoxy-3,3‑dimethylbutyro- tert-Butyl (4R,6R)-6‑cyanomethyl- nitrile, 97% nitrile, ≥99.0% (GC, sum of enan- 2,2‑dimethyl-1,3‑dioxane-4‑ace- tiomers) tate, 97% [84367‑31‑7] Cl CN C4H6ClNO OH [126567‑38‑2] [125971‑94‑0] O CN CH3 FW 119.55 O CH C8H13NO2 H C O t-Bu C14H23NO4 N C 3 3 CH 456152 FW 155.19 FW 269.34 OOO 3

00851 H3C CH3 (S)-(+)-2‑Methylbutyronitrile, 98% 539015 (R)-(+)-4‑Methylmandelonitrile, [25570‑03‑0] CN 97% ‑ C5H9N H3C N,O-Bis(4 methoxybenzyloxy- CH3 FW 83.13 ‑ ‑ carbonyl)-(S)-2‑amino-3- [10017 04 6] OH 247308 (4‑hydroxyphenyl)propionitrile, C9H9NO CN Organic Building Blocks FW 147.17 96% H3C (R)-(+)-4‑Chloromandelonitrile, 469734 O O 97% H3CO HN ‑ ‑ [97070 79 6] OH (R)-(+)-4‑Methoxymandelonitrile, O CN O C8H6ClNO CN 98% H CO O FW 167.59 3 Cl ‑ ‑ ‑ ‑ [97070 73 0] OH [73148 72 8] 469742 C H NO C H N O 9 9 2 CN 27 26 2 7 FW 163.17 FW 490.50 H3CO (R)-(+)-Mandelonitrile, 97% 370126 469688 ‑ ‑ [10020 96 9] OH C H NO 8 7 CN (R)-α-Acetoxyphenylacetonitrile, FW 133.15 ≥97.0% (GC, sum of enantiomers) 469653 ‑ ‑ [119718 89 7] CN O C10H9NO2 O CH3 FW 175.18

00873

Epoxides (S)-(−)-3,3,3‑Trifluoro-1,2‑epoxy- (S)-(+)-Epichlorohydrin, 98% (S)-(−)-Glycidol, 97% propane, 97% [67843‑74‑7] [60456‑23‑7] Cl OH [130025‑34‑2] C3H5ClO O C3H6O2 O F3C C3H3F3O O FW 92.52 FW 74.08 FW 112.05 540080 474789 665797 (R)-(+)-Propylene oxide, 99% (R)-(+)-Glycidol, 97% (R)-(+)-3,3,3‑Trifluoro-1,2‑epoxy- [15448‑47‑2] [57044‑25‑4] propane, 97% H3C OH C3H6O O C3H6O2 O [143142‑90‑9] FW 58.08 FW 74.08 F3C C3H3F3O O 540048 480819 FW 112.05 667005 (S)-(−)-Propylene oxide, 99% (R)-2‑Vinyloxirane, ≥95.0% (GC, sum of enantiomers) [16088‑62‑3] (R)-(−)-Epichlorohydrin, 99% H3C C3H6O [62249‑81‑4] O CH2 [51594‑55‑9] FW 58.08 C4H6O O Cl C3H5ClO O 540021 FW 70.09 FW 92.52 08011 540072

48 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (S)-3,4‑Epoxy-1‑butene, ≥90% (GC) Ethyl (S)-2‑oxiranylacetate, ≥96.0% (S)-2-(4‑Nitrophenyl)oxirane, (GC, sum of enantiomers) ≥98.0% (GC) [62249‑80‑3] CH2 C4H6O O [112083‑63‑3] [78038‑42‑3] O CH3 NO2 FW 70.09 C6H10O3 O O C8H7NO3

19377 FW 130.14 FW 165.15 O Blocks Building Organic 51241 Methyl (2S)-glycidate, 98% 75914 (R)-(+)-1,2‑Epoxyhexane, 97% ‑ ‑ ‑ [118712 39 3] O (R)-2-(4 Nitrophenyl)oxirane, C4H6O3 [104898‑06‑8] ≥ OCH3 CH3(CH2)2CH2 96.0% (GC) O FW 102.09 C6H12O O [78038‑43‑4] 469432 FW 100.16 NO2 C H NO 477087 8 7 3 FW 165.15 Methyl (2R)-glycidate, 97% O (S)-(+)-Glycidyl butyrate, 98% 69167 ‑ ‑ [111058 32 3] O ‑ ‑ C4H6O3 [65031 96 1] O OCH3 (R)-(+)-Styrene oxide, 97% O C7H12O3 FW 102.09 O CH3 FW 144.17 O ‑ ‑ 469424 [20780 53 4] 460508 C8H8O (S)-(−)-(2‑Bromoethyl)oxirane, FW 120.15 O − ≥90% (GC, sum of enantiomers) (R)-( )-Glycidyl butyrate, 96% 540099 ‑ ‑ [61847‑07‑2] [60456 26 0] O Br − C7H12O3 (S)-( )-Styrene oxide, 98% C4H7BrO O O CH3 FW 144.17 O FW 151.00 [20780‑54‑5]

16995 338125 C8H8O

FW 120.15 O (S)-4‑Chloro-1,2‑epoxybutane, (R)-(+)-1,2‑Epoxyheptane, ≥97.0% 540102 ≥98.0% (GC, sum of enantiomers) (GC, sum of enantiomers)

[948594‑94‑3] [110549‑07‑0] (2R,3R)-Diethyl 2,3‑epoxy- Cl CH2(CH2)3CH3 C4H7ClO O C7H14O O succinate, 96% FW 106.55 FW 114.19 [74243‑85‑9] 29177 49671 O O C8H12O5 H3C O O CH3 FW 188.18 O (S)-(−)-1,2‑Epoxybutane, 98% (R)-(+)-3‑Chlorostyrene oxide 586250 ‑ ‑ ‑ ‑ [30608 62 9] [62600 71 9] Cl H3C C4H8O O C8H7ClO (S)-N-Boc-2,3‑epoxypropylamine, FW 72.11 FW 154.59 97% 532363 O ‑ ‑ [161513 47 9] Boc 563382 N (R)-(+)-1,2‑Epoxybutane, 98% C8H15NO3 O H FW 173.21 ‑ ‑ (S)-(4‑Fluorophenyl)oxirane, [3760 95 0] 672033 H3C ≥ C4H8O O 95.0% (GC) FW 72.11 ‑ ‑ ‑ [134356 74 4] F (R)-(+)-1,2 Epoxyoctane, 97% 532355 C8H7FO [77495‑66‑0] FW 138.14 CH3(CH2)4CH2 O (R)-(−)-Glycidyl methyl ether, 97% C8H16O O 76477 FW 128.21 [64491‑70‑9] OCH3 477109 C H O O 4 8 2 (R)-(4‑Fluorophenyl)oxirane, FW 88.11 − ‑ ≥90.0% (GC) (2S,3S)-( )-3-(4 Nitrophenyl)glyci- 454680 dol, 98% ‑ ‑ [134356 73 3] F (S)-(+)-Glycidyl methyl ether, 97% [1885‑07‑0] C8H7FO O2N FW 138.14 C9H9NO4 ‑ ‑ O [64491 68 5] FW 195.17 OH OCH3 O C4H8O2 O 41609 FW 88.11 300500 454699

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 49 (R)-(−)-Glycidyl 3‑nitrobenzene- [3aS-(3aα,5aβ,6aβ,6bα)]-4‑Bromo- (2S)-(+)-Glycidyl tosylate, 98% sulfonate, ≥97.0% (GC) 3a,5a,6a,6b-tetrahydro- [70987‑78‑9] 2,2‑dimethyloxireno[e]-1,3‑benzo- O ‑ ‑ C H O S O S [115314 17 5] O 10 12 4 dioxole, 98% O O C9H9NO6S S NO2 FW 228.26 O CH3 O FW 259.24 O [130669‑74‑8] Br 540129 C9H11BrO3 O CH 50047 3 FW 247.09 O CH3 O (−)-Limonene oxide, mixture of cis (S)-(+)-Glycidyl 3‑nitrobenzene- 490857 and trans, 97% sulfonate, ≥99.0% (GC)

C10H16O H C ‑ ‑ [3aR-(3aα,5aβ,6aβ,6bα)]- 3 O [115314 14 2] O FW 152.23 C9H9NO6S O S NO2 3a,5a,6a,6b-Tetrahydro- O FW 259.24 O 2,2‑dimethyloxireno[e]-1,3‑benzodioxole, 96% H2C CH3 50048

Organic Building Blocks 218332 [145107‑27‑3] O CH3 (1S,2S)-(−)-1‑Phenylpropylene C9H12O3 O CH3 (+)-Limonene oxide, mixture of cis oxide, 98% FW 168.19 O and trans, 97% [4518‑66‑5] 490881 [1195‑92‑2] C H O H3C 9 10 H3C C H O O FW 134.18 tert-Butyldimethylsilyl (R)-(–)-gly- 10 16 O FW 152.23 cidyl ether, 98% 287792 H3C CH2 [124150‑87‑4] CH3 (1R,2R)-(+)-1‑Phenylpropylene C9H20O2Si t-Bu Si O 218324 O oxide, 97% FW 188.34 CH3 (+)-Limonene 1,2‑epoxide, ≥97.0% ‑ ‑ 684333 [14212 54 5] (GC, sum of isomers) C H O 9 10 H3C tert-Butyldimethylsilyl (S)-(+)-gly- FW 134.18 O [203719‑54‑4] H3C cidyl ether, 98% C H O O 277037 10 16 FW 152.23 [123237‑62‑7] CH3 t-Bu Si O − ‑ C9H20O2Si H3C CH2 (2S,3S)-( )-3 Phenylglycidol, 97% O FW 188.34 CH3 ‑ ‑ 17763 [104196 23 8] 684325 C9H10O2 OH (R)-(+)-1,2‑Epoxy-9‑decene, 97% FW 150.17 O (S)-(+)-Glycidyl benzyl ether, 99% 300489 [137310‑67‑9] [16495‑13‑9] CH2 O C10H18O O C H O O ‑ ≥ 10 12 2 FW 154.25 (S)-2 Oxiranylanisole, 97.0% FW 164.20 (GC, sum of enantiomers) 477281 363537 [71031‑03‑3] − ‑ − (2R)-( )-Glycidyl 4 nitrobenzoate, C9H10O2 (R)-( )-Glycidyl benzyl ether, 99% O 98% FW 150.17 O [14618‑80‑5] O ‑ ‑ [106268 95 5] O 04855 C10H12O2 O C H NO FW 164.20 10 9 5 O FW 223.18 O (R)-2‑Oxiranylanisole 363529 O2N

‑ ‑ 300438 [71031 02 2] (2R)-(−)-Glycidyl tosylate, 98% C9H10O2 O FW 150.17 ‑ ‑ (2S)-(+)-Glycidyl 4‑nitrobenzoate, O [113826 06 5] O C10H12O4S O S 98% 29438 FW 228.26 O O CH ‑ ‑ 3 [115459 65 9] O C10H9NO5 540110 O FW 223.18 O O2N

300446

50 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (2S)-(+)-2‑Methylglycidyl 4‑nitro- (R)-(+)-1,2‑Epoxydodecane, 97% (2R,3S)-(+)-3-(Benzyloxymethyl)ox- benzoate, 98% irane-2‑methanol 4‑nitrobenzoic [109856‑85‑1] CH2(CH2)8CH3 acid ester, ≥99.0% (HPLC, sum of ‑ ‑ C H O [118200 96 7] O 12 24 O CH enantiomers) 3 FW 184.32 C11H11NO5 O

FW 237.21 O 477141 Blocks Building Organic O2N O O O 305766 (R)-(+)-1,2‑Epoxytridecane, 97% O NO2 [59829‑81‑1] [78469‑86‑0] (2R)-(−)-2‑Methylglycidyl 4‑nitro- CH2(CH2)9CH3 C13H26O C18H17NO6 benzoate, 98% O FW 198.34 FW 343.33 ‑ ‑ [106268 96 6] O 477168 13730 CH3 C11H11NO5 O FW 237.21 O ′ ′ ′ ′ ′ − O2N (2 S,3 S)-4 -Bromo-cis-2 ,3 -epoxy- (2S,3R)-( )-3-(Benzyloxymethyl)ox- butyl (1S)-10‑camphorsulfonate, irane-2‑methanol 4‑nitrobenzoic 305758 98% acid ester, ≥99.0% (HPLC, sum of enantiomers) (2S,3S)-trans-3‑Methyloxirane- [343338‑27‑2] CH3 ‑ ‑ ≥ H3C 2 methyl 4 nitrobenzoate, 97.0% C14H21BrO5S O FW 381.28 (HPLC, sum of enantiomers) O O O O O S NO2 [106268‑97‑7] Br O H O O H O H3C [78513‑08‑3] C11H11NO5 O FW 237.21 O C18H17NO6 NO 510785 2 FW 343.33 68249 (R)-(+)-1,2‑Epoxytetradecane, 97% 13732

(R)-(−)-N-(2,3‑Epoxypropyl)phthal- [116619‑64‑8] CH2(CH2)10CH3 (R)-(+)-Glycidyl trityl ether, 98% imide, ≥99.0% (GC) C14H28O O FW 212.37 [65291‑30‑7] ‑ ‑ [181140 34 1] O 477176 C22H20O2 C11H9NO3 FW 316.39 O N FW 203.19 O O ‑ O (2S,3S)-1,2 Epoxy-3-(Boc-amino)- 4‑phenylbutane, 99% 671711 453455 ‑ ‑ [98737 29 2] H (S)-(+)-N-(2,3‑Epoxypropyl)phthal- C15H21NO3 O (S)-(−)-Glycidyl trityl ether, 98% FW 263.33 HN imide, ≥99.0% (GC) Boc [129940‑50‑7] [161596‑47‑0] 476951 O C22H20O2 C11H9NO3 N FW 316.39 O FW 203.19 ‑ O (R)-(+)-1,2 Epoxypentadecane, O O 97% 671606 [96938‑06‑6] CH2(CH2)11CH3 456268 C H O ‑ 15 30 O (2R)-(+)-3,3 Dimethylglycidyl FW 226.40 4‑nitrobenzoate, 98% 477184 ‑ ‑ [141700 91 6] O CH3 C12H13NO5 O CH FW 251.24 O 3 O2N

300535

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 51 Esters (+)-Methyl (R)-2‑chloropropionate, Methyl (S)-(+)-3‑hydroxybutyrate, Ethyl (R)-(+)-4,4,4‑trifluoro- 98% 99% 3‑hydroxybutyrate, 99%

‑ ‑ ‑ ‑ ‑ ‑ [77287 29 7] O [53562 86 0] OH O [85571 85 3] OH O C4H7ClO2 H3C C5H10O3 C6H9F3O3 OCH3 H3C OCH3 F3C O CH3 FW 122.55 Cl FW 118.13 FW 186.13 243167 376795 277754 − ‑ ‑ (−)-Methyl (S)-2‑chloropropionate, Methyl (R)-( )-3 hydroxy-2 methyl- Ethyl (R)-2-(trifluoromethylsul- ≥ 19 99% propionate, 99% fonyloxy)propionate, 97.0% ( F -NMR) ‑ ‑ ‑ ‑ [72657 23 9] O [73246 45 4] O C5H10O3 [84028‑89‑7] C4H7ClO2 H3C HO OCH3 O O OCH3 FW 118.13 CH3 C H F O S F C S O FW 122.55 Cl 6 9 3 5 3 OCH

Organic Building Blocks 3 O FW 250.19 CH3 247030 270148 91724 ‑ ‑ (−)-Methyl L-lactate, 98% Methyl (S)-(+)-3 hydroxy-2 methyl- propionate, 99% Ethyl (S)-2-(trifluoromethylsul- ‑ ‑ [27871 49 4] O ≥ ‑ ‑ fonyloxy)propionate, 96% C4H8O3 H3C [80657 57 4] O OCH3 C5H10O3 ‑ ‑ FW 104.10 OH HO OCH3 [84028 88 6] O O FW 118.13 CH3 F C S O C6H9F3O5S 3 OCH 230340 O 3 FW 250.19 CH 270121 3 (+)-Methyl D-lactate, 98% 374636 (−)-Ethyl L-lactate, 98% [17392‑83‑5] O (R)-(+)-2‑Methylsuccinic acid ‑ ‑ C4H8O3 HO [687 47 8] O OCH3 4‑methyl ester, 95% FW 104.10 CH C5H10O3 H3C 3 O CH3 FW 118.13 OH [81025‑83‑4] 277762 O H CO E34102 C6H10O4 3 OH FW 146.14 O CH3 (−)-Methyl (S)-3‑bromo-2‑methyl- ≥ propionate, 97% (+)-Ethyl D-lactate, 99.0% (GC, 546720 sum of enantiomers) ‑ ‑ [98190 85 3] O Dimethyl (S)-(−)-malate, 98% [7699‑00‑5] C5H9BrO2 O Br OCH3 C5H10O3 H3C ‑ ‑ FW 181.03 CH3 O CH3 [617 55 0] OH O FW 118.13 OH C H O H3CO 6 10 5 OCH 324922 3 69796 FW 162.14 O Methyl (R)-(+)-3‑bromo-2‑methyl- 374318 Dimethyl (4R,5R)-1,3,2‑dioxathio- propionate, 97% lane-4,5‑dicarboxylate 2,2‑dioxide, Dimethyl (R)-(+)-malate, 98% [110556‑33‑7] 97% O ‑ ‑ C H BrO [70681 41 3] OH O 5 9 2 Br OCH 3 ‑ ‑ H CO [117470 90 3] O O C6H10O5 3 FW 181.03 CH3 OCH3 C6H8O8S FW 162.14 O H3CO OCH3 325090 FW 240.19 O O S 455040 O O ‑ Methyl (R)-3 hydroxybutyrate, 441015 (−)-Dimethyl D-tartrate, 99% 99% ‑ [13171‑64‑7] ‑ ‑ Dimethyl (4S,5S)-1,3,2 dioxathio- OH O [3976 69 0] OH O C H O H3CO ‑ ‑ 6 10 6 OCH C5H10O3 lane-4,5 dicarboxylate 2,2 dioxide 3 H3C OCH3 FW 178.14 O OH FW 118.13 ‑ ‑ [127854 46 0] O O 243159 242942 C6H8O8S H3CO OCH3 FW 240.19 O O S O O

42544

52 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (+)-Dimethyl L-tartrate, 99% (+)-Methyl (S)-3‑hydroxyvalerate, Butyl (S)-(−)-lactate, 98% ≥98.0% (GC, sum of enantiomers) ‑ ‑ ‑ ‑ [608 68 4] O OH [34451 19 9] O C6H10O6 OCH3 [42558‑50‑9] C7H14O3 H3C H3CO OH O OCH3 FW 178.14 OH O C6H12O3 H3C FW 146.18 OH OCH3

FW 132.16 Blocks Building Organic 163457 420077 56657 Ethyl (R)-(+)-4‑bromo-3‑hydroxy- Isobutyl (R)-(+)-lactate, 97% (−)-Isopropyl L-lactate, ≥97.0% butyrate ‑ ‑ (GC, sum of enantiomers) [61597 96 4] O ‑ ‑ C7H14O3 H3C CH3 [95310 94 4] OH O O [63697‑00‑7] C6H11BrO3 Br O CH3 FW 146.18 OH CH3 O CH3 C6H12O3 H3C FW 211.05 O CH3 FW 132.16 OH 316598 542911 69807 (+)-tert-Butyl D-lactate, ≥99.0% Ethyl (S)-(−)-4‑bromo-3‑hydroxy- (GC, sum of enantiomers) butyrate Ethyl (R)-(−)-4‑cyano-3‑hydroxy- ‑ ‑ butyrate, 95% [68166 83 6] O ‑ ‑ CH [95537 36 3] OH O 3 C7H14O3 H3C O CH3 C6H11BrO3 Br [141942‑85‑0] O CH3 OH O FW 146.18 OH CH3 FW 211.05 C7H11NO3 N C O CH3 479608 FW 157.17 69806 479772 Ethyl (R)-(+)-4‑chloro-3‑hydroxy- (−)-Butyl L-lactate, ≥97.0% (GC, butyrate, 96% Dimethyl (R)-(+)-methylsuccinate, sum of enantiomers) 99% ‑ ‑ [34451‑19‑9] [90866 33 4] OH O O C H O H3C C6H11ClO3 Cl [22644‑27‑5] 7 14 3 OCH O CH3 O CH3 3 FW 146.18 OH FW 166.60 C7H12O4 OCH3 H3CO 460516 FW 160.17 O 69819 382094 Ethyl (S)-(−)-4‑chloro-3‑hydroxy- Ethyl (1R,2S)-cis-2‑hydroxycyclo- butyrate, 96% Methyl (R)-(+)-2,2‑dimethyl-1,3‑di- pentanecarboxylate, ≥97.0% (GC) ‑ [86728‑85‑0] oxolane-4 carboxylate, 98% ‑ ‑ OH O [61586 79 6] O C6H11ClO3 Cl O CH3 ‑ ‑ C8H14O3 [52373 72 5] O O CH3 FW 166.60 FW 158.19 C7H12O4 OCH 460524 3 OH FW 160.17 O O

H3C CH3 55170 Ethyl (R)-(−)-3‑hydroxybutyrate, 98% 345482 Ethyl (1S,2S)-trans-2‑hydroxycyclo- pentanecarboxylate, ≥97.0% [24915‑95‑5] (−)-Methyl (S)-2,2‑dimethyl-1,3‑di- OH O (GC, sum of enantiomers) C6H12O3 ‑ H3C O CH3 oxolane-4 carboxylate, 96% FW 132.16 [122331‑03‑7] ‑ ‑ O [60456 21 5] O 347329 C8H14O3 O CH3 C7H12O4 OCH3 FW 158.19 FW 160.17 OO OH Ethyl (S)-3‑hydroxybutyrate, 99% H C CH 3 3 19713 [56816‑01‑4] OH O 254606 C6H12O3 H3C O CH3 Methyl (4S)-(+)-2,2‑dimethyl- FW 132.16 Isobutyl (S)-2‑chloropropionate, 1,3‑dioxolane-4‑acetate, 97% 374709 ≥99.0% (GC, sum of enantiomers) [95422‑24‑5] OCH3 − ‑ ‑ ‑ C8H14O4 ( )-Methyl (R)-3 hydroxyvalerate, [83261 15 8] O OOO ≥ C H ClO H3CCH3 FW 174.19 98.0% (GC, sum of enantiomers) 7 13 2 O H3C CH3

FW 164.63 Cl CH3 [60793‑22‑8] OH O 441856 C6H12O3 H3C 51401 OCH FW 132.16 3 56655

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 53 (+)-Diethyl L-tartrate, ≥99% Methyl (S)-(+)-3-(2,2‑dimethyl- Benzyl (S)-(−)-lactate, 90% 1,3‑dioxolan-4‑yl)-cis-2‑prop- [87‑91‑2] [56777‑24‑3] OH O enoate, 85% O C8H14O6 H3C O C10H12O3 H3C O CH3 O FW 206.19 O OH [81703‑94‑8] FW 180.20 OH OCH3 C H O 156841 9 14 4 OO O 424846 FW 186.21 H3C CH3 (−)-Diethyl D-tartrate, ≥99% ‑ ≥ 347698 Methyl L-3 phenyllactate, 97.0% (HPLC) [13811‑71‑7] OH O − H3C O ( )-Dimethyl 2,3-O-isopropylidene- C8H14O6 O CH [13673‑95‑5] 3 O FW 206.19 O OH L -tartrate, 97% C10H12O3 OCH3 213969 ‑ ‑ FW 180.20 OH [37031 29 1] O O C9H14O6 H3CO OCH3 68193 tert-Butyl (R)-2‑hydroxybutyrate, FW 218.20 OO

Organic Building Blocks 98% H3C CH3 Methyl (2R,3S)-(+)-2,3‑dihydroxy- ‑ ‑ 359068 ‑ [206996 51 2] O 3 phenylpropionate, 99% CH3 C8H16O3 H3C O CH3 ‑ ‑ [122743 18 4] OH O FW 160.21 OH CH3 (+)-Dimethyl 2,3-O-isopropylidene- C10H12O4 D-tartrate, 98% OCH3 436984 FW 196.20 OH [37031‑30‑4] − ‑ O O 482919 ( )-tert-Butyl (S)-2 hydroxy- C9H14O6 H3CO OCH3 butyrate, 98% FW 218.20 OO Methyl (2S,3R)-(−)-2,3‑dihydroxy- H3C CH3 ‑ ‑ ‑ [37787 90 9] O 3 phenylpropionate, 99% CH3 384313 C8H16O3 H C O CH 3 3 [124649‑67‑8] FW 160.21 OH CH3 OH O ‑ C10H12O4 Ethyl (1R,2S)-cis-2 hydroxycyclo- OCH3 436976 hexanecarboxylate, ≥97.0% (GC) FW 196.20 OH ‑ ‑ ‑ 482927 (+)-tert-Butyl (S)-3 hydroxy- [61586 78 5] O butyrate, ≥96.0% (GC) C9H16O3 O CH3 ‑ FW 172.22 Methyl (R)-(+)-2-(4 hydroxyphen- ‑ ‑ OH [82578 45 8] OH O oxy)propionate, 98% CH3 C8H16O3 H C O CH 17887 3 3 [96562‑58‑2] FW 160.21 CH3 O C10H12O4 O Ethyl (1S,2S)-trans-2‑hydroxycyclo- OCH3 54953 FW 196.20 CH hexanecarboxylate, ≥95.0% (GC) HO 3 Methyl (R)-(−)-mandelate, ≥99% ‑ ‑ 472972 [29569 79 7] O C9H16O3 [20698‑91‑3] O CH3 OH FW 172.22 Ethyl (R)-cis-3-(2,2‑dimethyl-1,3‑di- C H O OCH3 OH 9 10 3 oxolan-4‑yl)propenoate, ≥98.0% FW 166.17 O 89472 (GC, sum of enantiomers) 251550 Ethyl (R)-(−)-mandelate, 99% [104321‑63‑3] C10H16O4 OO Methyl (S)-(+)-mandelate, ≥99% O O CH3 ‑ ‑ FW 200.23 [10606 72 1] OH H3C CH3 [21210‑43‑5] C10H12O3 O CH3 OH 59431 FW 180.20 O C9H10O3 OCH3 FW 166.17 O 309982 Ethyl (R)-(−)-3-(2,2‑dimethyl-1,3‑di- 251542 oxolan-4‑yl)-trans-2‑propenoate, Ethyl (S)-(+)-mandelate, 99% 97% ‑ Methyl (S)-(+)-3-(2,2 dimethyl- ‑ ‑ [13704 09 1] OH [104321‑62‑2] 1,3‑dioxolan-4‑yl)-trans-2‑prop- O C10H12O3 O CH3 C10H16O4 enoate, 93% O CH3 FW 180.20 O FW 200.23 OO ‑ ‑ H C CH [81703 93 7] O 309974 3 3 C9H14O4 OCH3 382442 FW 186.21 OO

H3C CH3

347965

54 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Ethyl (S)-(+)-3-(2,2‑dimethyl-1,3‑di- (+)-Methyl (R)-3-(1‑methyl-2‑oxo- Ethyl (R)-nipecotate, L-tartrate, oxolan-4‑yl)-2‑propenoate,pre- cyclohexyl)propionate, 99% 97% dominantly trans, 99% ‑ ‑ [94089 47 1] O O O O OH [64520‑58‑7] C11H18O3 OH O OCH3 O CH3 • HO CH 3 Blocks Building Organic C10H16O4 FW 198.26 OH O O CH3 N FW 200.23 OO H 302945 H3C CH3 [167392‑57‑6]

C12H21NO8 346810 Ethyl (S)-(−)-2-(tert-butyldimethyl- FW 307.30 silyloxy)propionate, 98% 472719 Diisopropyl (S)-(−)-malate, 99% [106513‑42‑2] CH3 O − [83541‑68‑8] C H O Si t-Bu Si O (1R)-( )-Neomenthyl acetate, 99% O CH3 11 24 3 O CH CH 3 C10H18O5 H3C O FW 232.39 3 CH O CH3 3 ‑ ‑ [146502 80 9] CH FW 218.25 CH O OH 3 3 C H O 424951 12 22 2 O 454877 FW 198.30 O CH3 − Methyl (S)-( )-4-(tert-butyl- H3C CH3 (−)-Diisopropyl D-tartrate, 98% dimethylsilyloxy)-2‑hydroxy- 420387 [62961‑64‑2] butanoate OH O CH3 C10H18O6 H3C O ‑ ‑ O CH3 [307532 01 0] OH (1S)-(+)-Neomenthyl acetate, 99% CH FW 234.25 CH3 O OH 3 C11H24O4Si HO O Si t-Bu [2552‑91‑2] FW 248.39 O CH CH3 227803 3 C12H22O2 O 648361 FW 198.30 O CH3 (+)-Diisopropyl L-tartrate, 99% H3C CH3 Ethyl (R)-(−)-2‑hydroxy-4‑phenyl- [2217‑15‑4] CH3 O OH butyrate, 98% 419990 C10H18O6 O CH3 H3C O FW 234.25 OH O CH3 ‑ ‑ [90315 82 5] OH (1R)-(−)-Menthyl acetate, 98% 229180 C12H16O3 O CH3 FW 208.25 O [2623‑23‑6] CH3 C H O Methyl (R)-3‑phenylbutyrate, 12 22 2 O 460826 FW 198.30 ≥99.0% (GC, sum of enantiomers) O CH3 ‑ H3C CH3 [1472‑07‑7] (5R,6R)-Dimethyl 5,6 dimethoxy- CH3 O 5,6‑dimethyl-1,4‑diox-2‑ene- 441058 C11H14O2 OCH3 FW 178.23 2,3‑dicarboxylate, 97% (1S)-(+)-Menthyl acetate, 99% 78275 C12H18O8 O CH O FW 290.27 3 O [5157‑89‑1] H3C OCH3 O H3C OCH3 C H O (+)-Ethyl (R)-3‑hydroxy-3‑phenyl- O 12 22 2 H C O CH CH O 3 3 ≥ 3 O FW 198.30 propionate, 99.0% (GC, sum of CH3

enantiomers) 556947 CH3

[72656‑47‑4] 441031 OH O (2R,3R,5R,6R)-Dimethoxy-5,6‑di- C11H14O3 O CH3 methyl-1,4‑dioxane-2,3‑dicarboxy- FW 194.23 (+)-Ethyl (S)-2‑hydroxy-4‑cyclo- lic acid dimethyl ester, 98% hexylbutyrate, ≥99.0% (GC, sum of 56187 ‑ ‑ [181586 74 3] O enantiomers) CH3O C12H20O8 O (−)-Ethyl (S)-3‑hydroxy-3‑phenyl- H3C OCH3 FW 292.28 H C OCH C12H22O3 OH ≥ 3 O 3 propionate, 97.0% (GC, sum of CH O FW 214.30 O CH3 3 O enantiomers) O 556920 ‑ ‑ 72437 [33401 74 0] OH O C11H14O3 O CH3 FW 194.23 (−)-Di-tert-butyl D-tartrate, 99%

56188 [117384‑46‑0] O OH CH3 CH3 C12H22O6 O CH3 H3C O CH3 FW 262.30 CH3 OH O

420018

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 55 (+)-Di-tert-butyl L-tartrate, 99% (R)-(−)-1‑Phenylethyl 3,5‑dinitro- (−)-Dibenzyl D-tartrate, ≥98.0% benzoate, 98% (HPLC, sum of enantiomers) [117384‑45‑9] O OH CH3 CH3 C12H22O6 O CH3 [3205‑33‑2] [4136‑22‑5] H3C O O CH3 O OH CH3 FW 262.30 CH3 OH O C15H12N2O6 O2N C18H18O6 O O O FW 316.27 FW 330.33 420026 OH O NO2 95352 tert-Butyl (S)-2‑hydroxyoctanoate, 461571 ≥97.0% (GC) (1R,2S,5R)-(+)-5‑Methyl-2-(1‑meth- ‑ ‑ (S)-(+)-1 Phenylethyl 3,5 dinitro- yl-1‑phenylethyl)cyclohexyl C12H24O3 O CH benzoate, 98% FW 216.32 3 chloroacetate, 99% H3C O CH3 OH CH3 [3205‑18‑3] ‑ ‑ O CH3 [71804 27 8] O C15H12N2O6 O2N 56067 O C18H25ClO2 Cl H C CH3 O FW 316.27 FW 308.84 3

NO2 Organic Building Blocks (+)-Dimethyl 2,3-O-benzylidene-D- CH3 tartrate, ≥98.0% (GC, sum of 461598 341363 enantiomers) Benzyl (R)-(−)-mandelate, 99% ‑ ‑ ‑ ‑ [91326 83 9] O (R)-(+)-1,1,2 Triphenyl-1,2 ethane- C13H14O6 O [97415‑09‑3] diol 2‑acetate, 97% OCH3 O FW 266.25 OCH C15H14O3 O 3 O ‑ ‑ [95061 47 5] O O FW 242.27 OH C22H20O3 H3C O 13476 456497 FW 332.39 OH Methyl (R)-(+)-3‑hydroxy-5‑oxo- Benzyl (S)-(+)-mandelate, 99% 1‑cyclopentene-1‑heptanoate, [62173‑99‑3] 376507 97% OH C15H14O3 O ‑ ‑ FW 242.27 − [41138 61 8] O O O ( )-Dimenthyl fumarate, 95% C13H20O4 OCH 3 458295 [34675‑24‑6] FW 240.30 CH3 HO C H O H3C CH3 24 40 4 O ‑ ‑ FW 392.57 O 463981 Benzyl (R)-(+)-2 hydroxy-3 phenyl- O O propionate, 97% H3C CH3 − ‑ ‑ CH3 Methyl (S)-( )-3 hydroxy-5 oxo- [7622‑22‑2] ‑ ‑ O 1 cyclopentene-1 heptanoate, C H O 348910 16 16 3 O 98% FW 256.30 OH ‑ ‑ (1S)-(+)-Dimenthyl succinate, 99% [42038 75 5] O O 461784 C13H20O4 [96149‑05‑2] OCH3 CH FW 240.30 3 − ‑ ‑ C24H42O4 H3C CH3 HO Benzyl (S)-( )-2 hydroxy-3 phenyl- O FW 394.59 O propionate, 97% O 473073 O H C CH [7622‑21‑1] 3 3 O CH3 − C H O ( )-Bis[(S)-1-(ethoxycarbonyl)ethyl] 16 16 3 O 306347 fumarate, 97% FW 256.30 OH

459879 − CH3 O O (1R)-( )-Dimenthyl succinate, 99% H3C O O O O CH3 O O CH ′ 3 (+)-Diisopropyl-O,O -bis(trimethyl- CH3 CH3 [111293‑23‑3] silyl)-L-tartrate, 99% O C14H20O8 ‑ ‑ O O [130678 42 1] CH3 O FW 316.30 H3C CH3 H3C CH3 C16H34O6Si2 H3C Si CH3 374792 FW 378.61 O O CH3 [34212‑59‑4] H3C O O CH3 C24H42O4 CH3 O O H3C Si CH3 FW 394.59 CH3 306355 420131

56 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Hydrocarbons (S)-(+)-1‑Bromo-2‑methylbutane, (+)-α-Pinene, ≥99% (+)-Camphene, 80% 99% [7785‑70‑8] [5794‑03‑6] CH

2 Blocks Building Organic [534‑00‑9] C10H16 C10H16 CH3 H3C CH H C Br FW 136.23 CH3 FW 136.23 3 C5H11Br 3 H3C H3C FW 151.04 268070 C301 250023 (−)-α-Pinene, 99% (−)-Camphene, 75% (90% as cam- (S)-(+)-1‑Iodo-2‑methylbutane, phene and fenchene) 99% [7785‑26‑4]

C10H16 H C [5794‑04‑7] ‑ ‑ 3 CH [29394 58 9] CH H C 3 3 FW 136.23 3 C10H16 H2C C H I H3C I 5 11 FW 136.23 H3C FW 198.05 305715 CH3 327131 (−)-β-Pinene, ≥99% 310425 ≥ (+)-Cuparene, 99.0% (GC, sum of ‑ ‑ ≥ [18172 67 3] CH (1R)-(+)-trans-Isolimonene, 95.0% enantiomers) H3C 3 C10H16 (GC, sum of enantiomers) [16982‑00‑6] FW 136.23 CH3 CH ‑ ‑ 2 [5113 87 1] CH C15H22 3 C10H16 FW 202.34 402753 H2C H3C FW 136.23 CH3 CH3 CH3 ‑ (1S)-(+)-3 Carene, 99% 58923 28255 ‑ ‑ [498 15 7] H H C CH3 (S)-(−)-Limonene, 96% C10H16 3 (S)-(+)-Citronellyl bromide, 95% H3C FW 136.23 H ‑ ‑ [5989 54 8] CH ‑ ‑ 3 [143615 81 0] CH CH C10H16 3 3 441619 H2C C10H19Br FW 136.23 H3C Br CH FW 219.16 3 (+)-2‑Carene, 97% 377716 218367 ‑ ‑ [4497 92 1] H H C CH3 (R)-(−)-Citronellyl bromide, 97% C10H16 3 (−)-β-Citronellene, ≥90% (GC, sum H3C FW 136.23 H of enantiomers) [10340‑84‑8] CH3 CH3 C H Br 232386 ‑ ‑ 10 19 H C Br [10281 56 8] 3 H3C CH FW 219.16 C10H18 2 CH3 CH3 377392 (1S,3R)-cis-4‑Carene, ≥97.0% FW 138.25 (GC, sum of enantiomers) 27477 (−)-Menthyl chloride, 98% [5208‑49‑1] CH3 (+)-Cyclosativene, 99% ‑ ‑ C10H16 [16052 42 9] CH 3 CH3 H3C C10H19Cl FW 136.23 ‑ ‑ H3C [22469 52 9] H3C FW 174.71 21987 C15H24 CH CH3 Cl H C 3 FW 204.35 3 CH3 249246 (1S,3S)-trans-4‑Carene, ≥85% H (GC, sum of enantiomers) 448559 (R)-(−)-α-Phellandrene, ≥95.0% (GC, sum of enantiomers) [5208‑50‑4] CH3 C10H16 CH3 [4221‑98‑1] H3C CH3 FW 136.23 C10H16 H3C FW 136.23 21989 CH3

77429

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 57 (−)-Isosativene, ≥97.0% (−)-β-Chamigrene, ~90% (3aR,6aR)-3,6-Diphenyl- 8 (GC, sum of enantiomers) (GC, sum of enantiomers) 1,3a,4,6a-tetrahydropenta- lene, 97% ‑ ‑ ‑ ‑ [24959 83 9] [18431 82 8] CH 2 [947503‑81‑3] C15H24 CH3 CH3 C15H24 H C CH3 FW 204.35 2 FW 204.35 C20H18 CH3 H H CH H3C 3 FW 258.36 59800 22480 H

(+)-Valencene, ≥70% 8 (3aS,6aS)-3,6-Diphenyl- 698725 [4630‑07‑3] 1,3a,4,6a-tetrahydropenta- lene, 97% C15H24 CH2 FW 204.35 CH3 H3C CH3 [940280‑80‑8]

C20H18 75056 H FW 258.36 Organic Building Blocks H

698733

Isocyanates/Isocyanides Methyl (S)-(−)-2‑isocyanato- (S)-(−)-α-Methylbenzyl isocyanate, (R)-(−)-1-(1‑Naphthyl)ethyl 3‑methylbutyrate, 99% 99% isocyanate, 98%

[30293‑86‑8] [14649‑03‑7] [42340‑98‑7] CH3 O NCO H3C NCO C7H11NO3 C9H9NO C13H11NO H3C OCH3 CH3 FW 157.17 NCO FW 147.17 FW 197.23

429805 220566 220442 (S)-(−)-α-Methylbenzyl isocyanide, ‑ Methyl (R)-(+)-2 isocyanato- (S)-(+)-1-(1‑Naphthyl)ethyl 96% ‑ 3 phenylpropionate, 97% isocyanate, 99% [21872‑32‑2] [361456‑36‑2] CH3 O [73671‑79‑1] H3C NCO C9H9N C H NO N C 11 11 3 OCH C H NO FW 131.17 3 13 11 FW 205.21 NCO FW 197.23

531324 562653 295957 (R)-(+)-α-Methylbenzyl isocyanate, Methyl (S)-(−)-2‑isocyanato- 99% 3‑phenylpropionate, 99%

[33375‑06‑3] ‑ ‑ CH3 [40203 94 9] O C9H9NO NCO C11H11NO3 OCH3 FW 147.17 FW 205.21 NCO

220574 409731

58 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Ketones (R)-(+)-3‑Methylcyclopentanone, (1R)-(+)-Nopinone, 98% (1R)-(−)-Camphorquinone, 99% 99% [38651‑65‑9] [10334‑26‑6] H3C CH3 H3C CH3 [6672‑30‑6] C9H14O C10H14O2 Blocks Building Organic CH3 O C6H10O FW 138.21 FW 166.22 FW 98.14 O H3C O O 327956 276286 M39709 (S)-(+)-2,3,7,7a-Tetrahydro-7a- (1S)-(+)-Camphorquinone, 99% (R)-5‑Hydroxy-2‑hexanone, ≥90% methyl-1H-indene-1,5(6H)-dione, [2767‑84‑2] (GC, sum of enantiomers) 97% H3C CH3 C10H14O2 CH3 ‑ ‑ O [65709 73 1] O [17553‑86‑5] FW 166.22 H3C O C6H12O2 H3C CH3 C10H12O2 O FW 116.16 OH FW 164.20 O 272078 79199 664073 (3aS,7aS)-(+)-Hexahydro-3a-hy- (1R,5S)-(+)-cis-Bicyclo[3.2.0]hept- (+)-3,9‑Dibromocamphor, 98% droxy-7a-methyl-1,5‑indandione, ‑ ‑ ≥ 2 en-6 one, 98.0% (GC, sum of 97% [10293‑10‑4] enantiomers) CH3 H C10H14Br2O Br [33879‑04‑8] OH [71155‑05‑0] O H FW 310.03 Br C10H14O3 H C C7H8O 3 O FW 182.22 FW 108.14 H3C O O H 306428 297933 67519 (R)-(−)-Carvone, 98% (+)-3‑Bromocamphor, ≥97.0% (GC, (−)-(1S,5R)-cis-Bicyclo[3.2.0]hept- [6485‑40‑1] CH3 sum of enantiomers) 2‑en-6‑one, ≥98.0% (GC, sum of C10H14O H C 2 O ‑ ‑ enantiomers) FW 150.22 [10293 06 8] CH CH3 H3C 3 C10H15BrO H [71155‑04‑9] H 124931 FW 231.13 Br H C C7H8O 3 O FW 108.14 O H (S)-(+)-Carvone, 96% 16571

69308 [2244‑16‑8] CH3 (R)-(+)-Pulegone, 98% C10H14O O (R)-(+)-3‑Methylcyclohexanone, FW 150.22 [89‑82‑7] O CH3 98% C10H16O H2C CH3 CH3 FW 152.23 ‑ ‑ H3C [13368 65 5] O 435759 C7H12O 376388 FW 112.17 CH3 (1S)-(−)-Verbenone, 94% (S)-(−)-Pulegone, 98% M38583 ‑ ‑ [1196 01 6] CH3 C10H14O [3391‑90‑0] H3C CH3 FW 150.22 C10H16O H C O 3 FW 152.23 O 218251 H3CCH3

328847

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 59 (−)-Pulegone, ≥98.0% (GC, sum of (1S)-(−)-Camphor, 99% (R)-(−)-8a-Methyl-3,4,8,8a-tetra- enantiomers) hydro-1,6(2H,7H)-naphthalene- [464‑48‑2] H3C CH3 dione, ≥98.0% (GC, sum of [3391‑90‑0] C10H16O CH3 CH3 O enantiomers) C10H16O FW 152.23 FW 152.23 ‑ ‑ O [100348 93 4] O 279676 H3C C11H14O2 H3CCH3 FW 178.23 ‑ ‑ O 82579 (S)-(+)-5-(1 Hydroxy-1 methyl- ‑ ‑ ethyl)-2 methyl-2 cyclohexen- 68169 ‑ (+)-Dihydrocarvone 1 one, 98% − ‑ [60593‑11‑5] (R)-( )-4,4a,5,6,7,8 Hexahydro-4a- [5524‑05‑0] CH3 CH3 C10H16O2 methyl-2(3H)-naphthalenone, C10H16O H3C H C O 2 O FW 168.23 ≥98.0% (GC, sum of enantiomers) FW 152.23 H3C OH CH3 [63975‑59‑7] 278807 CH3

Organic Building Blocks 37275 C11H16O FW 164.24 (1R,2R,5R)-(+)-2‑Hydroxy-3‑pina- O (+)-Fenchone, ≥98.0% (GC, sum of none, 99% enantiomers) 52560 [24047‑72‑1] ‑ ‑ CH3 − [4695 62 9] H3C ( )-3-(Trifluoroacetyl)camphor, CH3 C10H16O2 O C10H16O O 98% FW 168.23 CH FW 152.23 CH3 3 CH3 OH [207742‑84‑5] H3C CH3 400416 C12H15F3O2 CH3 46210 O FW 248.24 CF3 − ‑ ‑ (1R)-(−)-Fenchone, ≥98% (1S,2S,5S)-( )-2 Hydroxy-3 pina- O none, 99% [7787‑20‑4] 298344 ‑ ‑ C10H16O CH [1845 25 6] 3 H3C CH3 CH3 FW 152.23 CH3 C10H16O2 O (+)-3-(Trifluoroacetyl)camphor, H3C O FW 168.23 98% OH 196436 ‑ ‑ [51800 98 7] CH 380342 H3C 3 O C12H15F3O2 α,β-Thujone CF3 − FW 248.24 ( )-Menthone, 90% H3C O [76231‑76‑0] CH3 H3C [14073‑97‑3] 189006 C10H16O O CH3 O FW 152.23 C10H18O CH3 H CH3 FW 154.25 H3C (S)-(+)-Benzoin, 99% 283118 [5928‑67‑6] 218235 OH C14H12O2 − α ≥ FW 212.24 ( )- -Thujone, 96.0% (GC) (S)-(+)-3,4,8,8a-Tetrahydro-8a- O [546‑80‑5] methyl-1,6(2H,7H)-naphthalene- CH3 256250 H dione, 98% C10H16O O FW 152.23 [33878‑99‑8] (R)-(−)-Benzoin, 98% O H3C H3C CH3 C H O 11 14 2 [5928‑66‑5] FW 178.23 OH 89231 O C14H12O2

FW 212.24 O (1R)-(+)-Camphor, 98% 437026 459941 [464‑49‑3] H3C CH3 C10H16O FW 152.23 H C 3 O

857300

60 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. 3-(Perfluorobutyryl)-(−)-camphor, Irone, ≥90% (GC) (−)-Isolongifolen-9‑one, ≥99.5% 98% (GC, sum of enantiomers) [79‑69‑6] CH CH3 ‑ ‑ C H O H3C 3 ‑ ‑ [115224 00 5] CH 14 22 H3C [26839 52 1] H3C 3 O H3C CH3 C14H15F7O2 FW 206.32 C15H22O O CH3 CH O 3 FW 348.26 F F FW 218.33 Blocks Building Organic CF 3 58220 H3C CH3 O F F 58926 298336 5-[3,4-(Dimethoxy)phenyl]- 1,3‑cyclohexanedione, 98% 7‑Acetyl-5,8‑dihydroxy-4‑iso- 3-(Perfluorobutyryl)-(+)-camphor, [190064‑28‑9] propyl-1‑methylbicyclo[4.3.0]non- H3CO 96% C H O 14 16 4 O ane, 97% FW 248.27 H3CO [51800‑99‑8] H C CH3 [457949‑49‑4] 3 O F F CH3 C14H15F7O2 O OH C15H26O3 CF3 FW 348.26 CH3 F F 539902 FW 254.37 H3C H3C O OH O CH3 195936 ≥ (+)-Nootkatone, 99.0% (GC) 541699 [4674‑50‑4] H C CH3 3 CH3 C15H22O CH FW 218.33 2 O

74437

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 61 Lactams/Lactones (R)-4-(Trichloromethyl)-2‑oxeta- (S)-(−)-4‑Methyl-4-(trichloro- (S)-(+)-Pantolactone, 99% none, ≥99.0% (GC) methyl)-2‑oxetanone, 98% [5405‑40‑3] H3C OH [20710‑33‑2] [93206‑60‑1] C6H10O3 H C H3C 3 Cl3C O O FW 130.14 C4H3Cl3O2 O C5H5Cl3O2 Cl3C O O O FW 189.42 FW 203.45 437328 91292 340243 − α ε (S)-(−)-4‑Oxo-2‑azetidinecarboxylic (R)-γ-Valerolactone, ≥97.0% (GC) L-( )- -Amino- -caprolactam ≥ acid, 98% hydrochloride, 97.0% (AT) [58917‑25‑2] [26081‑07‑2] ‑ ‑ C5H8O2 H3C O [16404 94 7] O O NH2 O C6H12N2O · HCl C4H5NO3 FW 100.12 • HCl N OH FW 164.63 N O FW 115.09 H 43948 H Organic Building Blocks 473278 21612 (1S)-(+)-2‑Azabicyclo[2.2.1]hept- (R)-(+)-α-Hydroxy-γ-butyrolactone, 5‑en-3‑one, ≥98% (1S,5R)-2‑Oxabicyclo[3.3.0]oct- 97% 6‑en-3‑one, 99% [130931‑83‑8] O [56881‑90‑4] C6H7NO [43119‑28‑4] OH N H FW 109.13 H C4H6O3 C7H8O2 O O FW 102.09 O 441287 FW 124.14 O H 444286 (1R)-(−)-2‑Azabicyclo[2.2.1]hept- 448478 (S)-(−)-α-Hydroxy-γ-butyrolactone, 5‑en-3‑one, ≥98% ‑ 97% (1R,5S)-3 Oxabicyclo[3.3.0]oct- [79200‑56‑9] 6‑en-2‑one, ≥95.0% (GC) ‑ ‑ C6H7NO NH [52079 23 9] OH FW 109.13 [128946‑78‑1] C4H6O3 O O FW 102.09 O O C7H8O2 441279 FW 124.14 O 444235 (3S)-cis-3,6‑Dimethyl-1,4‑dioxane- 75653 (S)-β-Hydroxy-γ-butyrolactone, 2,5‑dione, 98% 96% (R)-(−)-γ-Ethoxycarbonyl-γ-butyro- [4511‑42‑6] H3C O O lactone, 95% [7331‑52‑4] HO C6H8O4 O O CH C4H6O3 FW 144.13 3 [33019‑03‑3] O FW 102.09 O C H O O OCH3 367044 7 10 4 O 422797 FW 158.15 O (R)-5‑Hexanolide, ≥95.0% (GC, sum 346969 − α γ (S)-( )- -Amino- -butyrolactone of enantiomers) hydrobromide, 99% (3aR,4S,5R,6aS)-(−)-Hexahydro- [43112‑32‑9] 5‑hydroxy-4-(hydroxymethyl)-2H- [15295‑77‑9] O C6H10O2 ‑ H3C O O cyclopenta[b]furan-2 one, 98% C4H7NO2 · HBr FW 114.14 O NH2 • HBr FW 182.02 ‑ ‑ 94154 [32233 40 2] OH C H O 471429 8 12 4 FW 172.18 O OH D-(−)-Pantolactone, 99% O ‑ (R)-(+)-4 Methyl-4-(trichloro- ‑ ‑ [599 04 2] H C 341576 methyl)-2‑oxetanone, 98% 3 OH C6H10O3 H3C ‑ ‑ FW 130.14 O O [93239 42 0] H C 3 O C5H5Cl3O2 Cl3C O 237817 FW 203.45 340235

62 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (3aS,4R,5S,6aR)-(+)-Hexahydro- (+)-2,3‑Cyclohexylidene-L-erythrur- (+)-Corey lactone, 4‑phenylbenzo- 5‑hydroxy-4-(hydroxymethyl)-2H- onic acid, 96% ate alcohol, 99% cyclopenta[b]furan-2‑one, 98% [85281‑85‑2] [39265‑57‑1] O H H OH [76704‑05‑7] C10H14O5 O C21H20O5 OH O O O

O Blocks Building Organic C8H12O4 O OH FW 214.22 O FW 352.38 H H O FW 172.18 O HO 453218 536245 453226

(R)-α-Acryloyloxy-β,β-dimethyl-γ- Benzyl (S)-(−)-4‑oxo-2‑azetidine- (−)-Corey lactone, 4‑phenylbenzo- butyrolactone, 95% carboxylate, 97% ate alcohol, 99% ‑ ‑ ‑ ‑ [31752‑99‑5] [102096 60 6] H C [72776 05 7] O H 3 O OH CH C H NO C21H20O5 C9H12O4 H3C 2 11 11 3 O O O O O O FW 184.19 O FW 205.21 N FW 352.38 O H H O

376361 468975 249262

(R)-2-tert-Butyl-6‑methyl-1,3‑diox- (R)-(−)-Dihydro-5-(p-tolylsulfonyl- (S)-(+)-γ-Trityloxymethyl-γ-butyro- in-4‑one, ≥99.0% (HPLC, sum of oxymethyl)-2(3H)-furanone, 98% lactone, 98% enantiomers) ‑ ‑ [58879 33 7] O [73968‑62‑4] [107289‑20‑3] C12H14O5S S t-Bu O O C24H22O3 O O C9H14O3 FW 270.30 FW 358.43 O O CH3 O O FW 170.21 H O H C O 3 364541 20264 (S)-(+)-Dihydro-5-(p-tolylsulfonyl- 371521 ‑ oxymethyl)-2(3H)-furanone, 98% (2R,6R)-2-tert-Butyl-6 methyl- − γ γ ‑ ‑ ≥ (R)-( )- -Trityloxymethyl- -butyro- 1,3 dioxan-4 one, 98.5% (GC, sum ‑ ‑ [58879 34 8] O lactone, 98% of enantiomers) C H O S O S CH3 12 14 5 O O O ‑ ‑ ‑ ‑ FW 270.30 [78158 90 4] [100017 18 3] O C24H22O3 C H O 364568 O 9 16 3 O FW 358.43 O FW 172.22 O H3C O t-Bu [3R(1′R,4R)]-(+)-4‑Acetoxy-3-[1- 20260 (tert-butyldimethylsilyloxy)ethyl]- 2‑azetidinone, 98% 438979 (1R)-(+)-Camphanic acid, 98% [76855‑69‑1] CH3 [67111‑66‑4] C13H25NO4Si H3C O Si t-Bu H3C CH3 O H CH3 C10H14O4 CH3 FW 287.43 O H3C O O FW 198.22 N O H O OH 375845 382418

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 63 Polyamines (R)-(+)-1,2‑Diaminopropane dihy- (1R,2R)-(−)-1,2‑Diaminocyclo- (1R,2R)-(+)-1,2‑Diaminocyclo- drochloride, 99% hexane, 98% hexane L-tartrate, 99%

[19777‑67‑4] [20439‑47‑8] [39961‑95‑0] NH2 • 2HCl NH2 NH2 OH O C3H10N2 · 2HCl NH2 C6H14N2 C10H20N2O6 • HO H3C OH NH FW 147.05 FW 114.19 2 FW 264.28 NH2 O OH 412554 346721 416932 − ‑ (S)-( )-1,2 Diaminopropane dihy- (1S,2S)-(+)-1,2‑Diaminocyclo- (1S,2S)-(−)-1,2‑Diaminocyclo- drochloride, 99% hexane, 98% hexane D-tartrate, 99% [19777‑66‑3] ‑ ‑ H3C [21436 03 3] NH [67333‑70‑4] NH2 • 2HCl 2 NH2 O OH C3H10N2 · 2HCl NH2 C6H14N2 C H N O OH 10 20 2 6 • HO FW 147.05 NH2 NH FW 114.19 FW 264.28 2 OH O Organic Building Blocks 412562 346713 416940 (R)-(+)-Propylenediamine dihydro- − ′ ‑ (R,R)-( )-N,N -Dimethyl-1,2 cyclo- (1R,2R)-(+)-1,2‑Diphenylethylene- chloride, ≥98.0% (TLC/AT) ≥ hexanediamine, 97.0% (GC) diamine, 97% ‑ ‑ [19777 67 4] NH • 2HCl ‑ ‑ 2 [68737 65 5] H NH [35132‑20‑8] C3H10N2 · 2HCl 2 N NH H3C C8H18N2 CH3 2 FW 147.05 C14H16N2 FW 142.24 N CH3 H FW 212.29 82253 NH2

671274 364010 (1S,2S)-trans-1,2‑Cyclopentanedi- ′ ‑ amine dihydrochloride, 99% (S,S)-(+)-N,N -Dimethyl-1,2 cyclo- (1S,2S)-(−)-1,2‑Diphenylethylenedi- hexanediamine, ≥97.0% (GC) [477873‑22‑6] amine, 97% NH2 C5H12N2 · 2HCl ‑ ‑ • 2HCl [87583 89 9] H [29841‑69‑8] NH2 N NH FW 173.08 C8H18N2 CH3 2 C14H16N2 CH 670219 FW 142.24 N 3 FW 212.29 H NH2

(1R,2R)-trans-1,2‑Cyclopentanedi- 669660 364002 amine dihydrochloride, 99%

C5H12N2 · 2HCl NH2 FW 173.08 • 2HCl NH2

670324

64 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. Polyols (R)-(−)-3‑Chloro-1,2‑propanediol, (2R,3R)-(−)-2,3‑Butanediol, 97% (S)-2‑Methyl-1,4‑butanediol, 97% ≥97.0% (GC, sum of enantiomers) ‑ ‑ [24347 58 8] OH [57090‑45‑6] C4H10O2 H3C [70423‑38‑0] Blocks Building Organic OH CH3 HO OH C3H7ClO2 Cl OH FW 90.12 OH C5H12O2 CH3 FW 110.54 FW 104.15 237639 540056 53586 (R)-(+)-1,2,4‑Butanetriol, 98% (S)-(+)-3‑Chloro-1,2‑propanediol, (1S-cis)-3‑Bromo-3,5‑cyclohexa- ‑ ‑ 97% [70005 88 8] OH diene-1,2‑diol, 96% OH C4H10O3 HO [60827‑45‑4] [130792‑45‑9] Cl OH FW 106.12 OH C3H7ClO2 OH 309710 C6H7BrO2 FW 110.54 FW 191.02 OH Br 540064 − ‑ (S)-( )-1,2,4 Butanetriol, 98% 489492 (R)-(−)-1,2‑Propanediol, 96% [42890‑76‑6] OH ‑ C4H10O3 OH (1S,2S)-trans-1,2 Cyclohexanediol, ‑ ‑ HO [4254 14 2] H C FW 106.12 99% 3 OH C3H8O2 OH 296678 ‑ ‑ FW 76.09 [57794 08 8] OH 540242 ‑ C6H12O2 (1R,2R)-(-)-trans-1,2 Cyclopentane- FW 116.16 OH diol, 98% (S)-(+)-1,2‑Propanediol, 96% 421804 [930‑46‑1] ‑ ‑ OH [4254 15 3] H C (1R,2R)-trans-1,2‑Cyclohexanediol, 3 C5H10O2 OH C H O OH 3 8 2 OH FW 102.13 99% FW 76.09 459259 ‑ ‑ 540250 [1072 86 2] OH C6H12O2 ‑ OH (S)-3‑Butene-1,2‑diol, ≥97.0% (GC) (1S,2S)-(+)-trans-1,2 Cyclopentane- FW 116.16 diol, 98% 421790 [62214‑39‑5] OH H2C [63261‑45‑0] C4H8O2 OH OH (2S,5S)-2,5‑Hexanediol, 99% FW 88.11 C5H10O2 OH FW 102.13 ‑ ‑ 19159 [34338 96 0] OH C6H14O2 H3C 459267 CH3 (R)-(−)-1,3‑Butanediol, 98% FW 118.17 OH − ‑ ‑ ‑ (R,R)-( )-2,4 Pentanediol, 99% 396729 [6290 03 5] OH

C4H10O2 H C OH [42075‑32‑1] 3 OH OH ‑ ≥ FW 90.12 (2R,5R)-2,5 Hexanediol, 99.0% C5H12O2 H3C CH3 237612 FW 104.15 (GC, sum of enantiomers) 243175 [17299‑07‑9] ‑ OH (S)-(+)-1,3 Butanediol, 98% C6H14O2 H3C CH3 ‑ ‑ (2S,4S)-(+)-Pentanediol, 99% FW 118.17 OH [24621 61 2] OH C4H10O2 ‑ ‑ 52792 H3C OH [72345 23 4] OH OH FW 90.12 C5H12O2 H3C CH3 237620 FW 104.15 (R)-(−)-2‑Methyl-2,4‑pentanediol, 267872 99% (2S,3S)-(+)-2,3‑Butanediol, 97% [99210‑90‑9] (R)-2‑Methyl-1,4‑butanediol, H3C OH OH [19132‑06‑0] C6H14O2 OH ≥98.0% (GC, sum of enantiomers) H3C CH3 C4H10O2 H3C FW 118.17 CH3 FW 90.12 OH ‑ ‑ 252840 [22644 28 6] HO OH C5H12O2 300349 CH3 FW 104.15 04964

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 65 (R)-(+)-3,3‑Difluoro-1,2‑heptane- (R)-(+)-1‑Phenyl-1,3‑propanediol, (R)-(+)-1,2‑Decanediol, 99% diol, 95% ≥99.0% (GC, sum of enantiomers) ‑ ‑ [87827 60 9] OH ‑ ‑ [103548‑16‑9] C10H22O2 OH [158358 96 4] OH OH CH3(CH2)6CH2 C H F O HO C H O FW 174.28 7 14 2 2 CH3 9 12 2 OH FW 168.18 F F FW 152.19 483303

477427 78917 (S)-(−)-1,2‑Decanediol, 99% D-Pinitol, 95% α α α α ‑ ‑ ‑ [3aS-(3a ,4 ,5 ,7a )]-7 Bromo- [84276 14 2] OH 3a,4,5,7a-tetrahydro-2,2‑dimethyl- C10H22O2 OH [10284‑63‑6] CH3(CH2)6CH2 OH ‑ ‑ FW 174.28 C7H14O6 HO OH 1,3 benzodioxole-4,5 diol, 99% FW 194.18 482218 HO OH ‑ ‑ [130669 72 6] Br OCH3 C H BrO O 9 13 4 CH3 (3S,6S)-2,7‑Dimethyl-3,6‑octane- FW 265.10 441252 HO O CH3 diol, ≥99.0% (GC, sum of enan- OH Organic Building Blocks tiomers) (2R,6R)-2,6‑Heptanediol, ≥99.0% 490350 (GC, sum of enantiomers) [129705‑30‑2] CH3 OH C H O CH [3aS-(3aα,4α,5α,7aα)]-3a,4,5,7a- 10 22 2 3 ‑ ‑ H3C [143170 07 4] OH OH FW 174.28 Tetrahydro-2,2‑dimethyl- OH CH3 C7H16O2 H3C CH3 ‑ ‑ FW 132.20 1,3 benzodioxole-4,5 diol, 98% 39277 40617 [130669‑76‑0] O CH3 − ‑ C9H14O4 (2R,3R)-( )-2 Benzyloxy- O (S)-(+)-1-(2‑Chlorophenyl)- FW 186.21 HO CH3 1,3,4‑butanetriol OH 1,2‑ethanediol, 96% ‑ ‑ 490385 [84379 52 2] HO ‑ ‑ C H O [133082 13 0] OH 11 16 4 O OH C H ClO OH FW 212.24 8 9 2 (R)-(−)-1,3‑Nonanediol, 97% OH FW 172.61 Cl ‑ ‑ 13624 [121541 65 9] OH 494194 C9H20O2 CH3(CH2)4CH2 OH FW 160.25 (R)-(−)-1-(2‑Naphthyl)-1,2‑ethane- (R)-(−)-1‑Phenyl-1,2‑ethanediol, 538981 diol, 98% 99% ‑ ‑ ‑ ‑ [49801 14 1] OH [16355‑00‑3] (1R,2S)-cis-1,2 Dihydro-1,2 naph- OH C12H12O2 OH OH thalenediol, ≥98.0% (GC) C8H10O2 FW 188.22 FW 138.16 ‑ ‑ [51268 88 3] OH 482862 302163 C10H10O2 OH FW 162.19 (S)-(+)-1-(2‑Naphthyl)-1,2‑ethane- (S)-(+)-1‑Phenyl-1,2‑ethanediol, 37342 diol, 98% 99% ‑ ‑ [43210 74 8] OH [25779‑13‑9] (1R,2R,3S,5R)-(−)-Pinanediol, 99% OH C12H12O2 OH C8H10O2 OH ‑ ‑ FW 188.22 [22422 34 0] H C FW 138.16 3 CH C H O 3 10 18 2 482870 FW 170.25 CH3 302155 OH OH (1S-cis)-3‑Phenyl-3,5‑cyclohexa- (3R,6R)-3,6‑Octanediol, ≥98.0% 287784 diene-1,2‑diol, 98% (GC, sum of enantiomers) ‑ ‑ (1S,2S,3R,5S)-(+)-Pinanediol, 99% [66008 24 0] OH ‑ ‑ OH [129619 37 0] OH C12H12O2 C8H18O2 H3C [18680‑27‑8] FW 188.22 CH3 H3C CH3 FW 146.23 OH C10H18O2 H FW 170.25 18717 HO H3C 489638 OH

282367

66 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (R,R)-(−)-1‑Phenylcyclohexane-cis- (1R,2R)-1,2‑Dicyclohexyl- (S,S)-(−)-1-(1‑Naphthyl)-2-(2‑naph- 1,2‑diol, 99% 1,2‑ethanediol, 95% thyl)-1,2‑ethanediol, 98%

[125132‑75‑4] [120850‑92‑2] [229185‑00‑6] OH OH HO C12H16O2 C14H26O2 C22H18O2

FW 192.25 FW 226.36 OH FW 314.38 OH Blocks Building Organic OH

482935 400149 482854

(S,S)-(+)-1‑Phenylcyclohexane-cis- (S)-(−)-1,1‑Diphenyl-1,2‑propane- (S,S)-(−)-1,2‑Di(1‑naphthyl)- 1,2‑diol, 99% diol, 99% 1,2‑ethanediol, 98% ‑ ‑ [46755‑94‑6] [229184‑99‑0] [34281 90 8] OH OH HO C H O H3C C H O C12H16O2 15 16 2 OH 22 18 2 FW 192.25 FW 228.29 FW 314.38 OH OH 482846 482943 364908 ‑ ‑ ‑ (R)-(+)-1,2‑Dodecanediol, 99% (S)-(−)-1,1,2‑Triphenyl-1,2‑ethane- (+)-1,6 Bis-(2 chlorophenyl)-1,6 di- ‑ ‑ diol, 99% phenyl-2,4 hexadiyne-1,6 diol, ‑ ‑ ≥ [85514 84 7] OH 99.0% (HPLC, sum of enantiom- C12H26O2 OH [108998‑83‑0] CH3(CH2)8CH2 OH ers) FW 202.33 C20H18O2 ‑ ‑ 482234 FW 290.36 HO [86436 19 3] C30H20Cl2O2 FW 483.38 (S)-(−)-1,2‑Dodecanediol, 99% HO OH 367435 Cl Cl ‑ ‑ [85514 85 8] OH C12H26O2 OH Sclareol CH3(CH2)8CH2 14662 FW 202.33 [515‑03‑7] 482226 CH2 H C CH C20H36O2 3 HO 3 (−)-1,6‑Bis(2‑chlorophenyl)-1,6‑di- OH H FW 308.50 CH3 phenyl-2,4‑hexadiyne-1,6‑diol (S,S)-(−)-Hydrobenzoin, 99% H C CH 3 3 [96158‑84‑8] [2325‑10‑2] OH 357995 C30H20Cl2O2 C14H14O2 FW 483.38 HO OH FW 214.26 OH (R,R)-(+)-1,2‑Di(1‑naphthyl)- Cl Cl 256269 1,2‑ethanediol, 98% C1662 [116204‑39‑8] (R,R)-(+)-Hydrobenzoin, 99% OH C22H18O2

[52340‑78‑0] FW 314.38 OH OH C14H14O2 482900 FW 214.26 OH

256277

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 67 Protected Alcohols/Amines (R)-(+)-4-(Chloromethyl)-2,2‑di- (−)-Dihydrocarvyl acetate, ≥95% (1R,2R)-(−)-N-p-Tosyl-1,2‑cyclo- methyl-1,3‑dioxolane, 98% hexanediamine, 97% [20777‑49‑5] CH3 [57044‑24‑3] C12H20O2 C H N O S Cl H2C 13 20 2 2 O O CH3 H C H ClO FW 196.29 N S CH3 6 11 2 OO CH FW 268.38 3 O O FW 150.60 H3C CH3 NH2 194107 456136 677302 ‑ ‑ ‑ − ‑ (R)-(+)-4 Hexyl-2,2 dimethyl-1,3 di- (S)-( )-4-(Chloromethyl)-2,2 di- (1S,2S)-(+)-N-p-Tosyl-1,2‑cyclo- ‑ oxane, 98% methyl-1,3 dioxolane, 98% hexanediamine, 97% [139008‑44‑9] ‑ ‑ O [60456 22 6] CH Cl 3 C13H20N2O2S O C12H24O2 H C6H11ClO2 OO CH3(CH2)4CH2 O CH3 FW 200.32 FW 268.38 N S CH3 O Organic Building Blocks FW 150.60 H3C CH3 539678 NH2 456144 677310 (S)-4‑Benzyloxymethyl-2,2‑dimeth- (R)-5‑Acetoxy-1‑chlorohexane, yl-1,3‑dioxolane, ≥95.0% (GC, sum (S)-(−)-1,2‑Propanediol di-p-tosy- 99% of enantiomers) late, 99% ‑ ‑ ‑ ‑ [154885 34 4] O [16495 03 7] O O C8H15ClO2 C13H18O3 O O O H3C O O S S O FW 178.66 FW 222.28 H3C CH3 O H3C Cl O CH3 CH3 H3C 531529 59442 [60434‑71‑1] − ‑ ‑ C17H20O6S2 (1R,2R)-trans-N-Boc-1,2‑cyclo- (R)-( )-2,2 Dimethyl-1,3 dioxolan- ‑ FW 384.47 hexanediamine, 97% 4 ylmethyl p-toluenesulfonate, 97% 309656 ‑ ‑ [146504 07 6] NH 2 ‑ ‑ − ‑ C11H22N2O2 [23788 74 1] O ( )-2,3 Butanediyl di(p-toluene- Boc N C13H18O5S O S CH3 FW 214.30 H sulfonate), 99% O FW 286.34 O O 670650 H3C CH3 O CH 3 O S O O S 337412 O (1S,2S)-trans-N-Boc-1,2‑cyclo- CH3 O H3C hexanediamine, 97% CH3 (S)-(+)-2,2‑Dimethyl-1,3‑dioxolan- [74839‑83‑1] [180683‑64‑1] ‑ NH2 4 ylmethyl p-toluenesulfonate, C18H22O6S2 C11H22N2O2 Boc 97% FW 398.49 N FW 214.30 H 310522 ‑ ‑ [23735 43 5] O 670766 C13H18O5S O S CH3 O (1R,2R)-(+)-N,N′-Di-p-tosyl- FW 286.34 O O (−)-Bornyl acetate, 95% 1,2‑cyclohexanediamine, 98% H3C CH3

[5655‑61‑8] O O H C CH3 337420 3 S NH HN S C12H20O2 O O FW 196.29 H3C CH3 CH3 H3C O [143585‑47‑1] O C20H26N2O4S2 B55203 FW 422.56 482757

68 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (1S,2S)-(−)-N,N′-Di-p-tosyl- (1R,2R)-(−)-N-p-Tosyl-1,2‑diphenyl- (1S,2S)-(+)-N-p-Tosyl-1,2‑diphenyl- 1,2‑cyclohexanediamine, 98% ethylenediamine, 98% ethylenediamine, 98% ‑ ‑ ‑ ‑ O O [144222 34 4] NH O [167316 27 0] NH O 2 H 2 H S NH HN S C21H22N2O2S N S C21H22N2O2S N S O O O O FW 366.48 FW 366.48 Blocks Building Organic H3C CH3 CH3 CH3

[212555‑28‑7] 484334 484342 C20H26N2O4S2 FW 422.56 482765

Sulfonamides/Sulfinamides

(R)-(−)-p-Toluenesulfinamide, 98% (S)-(−)-N-[1-(Hydroxymethyl)- (−)-10‑Dicyclohexylsulfamoyl-D-iso- 2‑phenylethyl]-4‑methylbenzene- borneol, 98% [247089‑85‑6] O sulfonamide, 97% C H NOS S ‑ ‑ 7 9 [99295 72 4] CH NH2 H3C 3 FW 155.22 ‑ ‑ C H NO S H C [82495 70 3] O 22 39 3 3 H C16H19NO3S S N FW 397.61 HO O 520497 FW 305.39 O S N H3C HO O

(S)-(+)-p-Toluenesulfinamide, 98% 470600 297658 [188447‑91‑8] O (R,R)-(+)-N,N′-Bis(α-methylbenzyl) C7H9NOS S NH2 sulfamide, 99% (+)-N,N-Dicyclohexyl-(1R)-isobor- FW 155.22 H3C neol-10‑sulfonamide, 98% [91410‑68‑3] CH O CH3 516899 3 C16H20N2O2S S [96303‑88‑7] N N H C CH3 H O H 3 FW 304.41 C22H39NO3S ′ ‑ (1R)-trans-N,N -1,2 Cyclohexane- FW 397.61 O OH diylbis(1,1,1‑trifluoromethane- 276081 N S O sulfonamide), 97% (S,S)-(−)-N,N′-Bis(α-methylbenzyl) [122833‑60‑7] CF3 sulfamide, 99% 305790 C8H12F6N2O4S2 O S O NH [27304‑75‑2] FW 378.31 CH3 CH ‑ O O 3 (1R,exo,exo)-3-[N-(3,5 Dimethyl- C16H20N2O2S N S CF3 N S N H phenyl)benzenesulfonamido]iso- O FW 304.41 H H O borneol, ≥98.5% (HPLC, sum of 433721 276073 enantiomers)

‑ [87420‑26‑6] (1S)-10 Camphorsulfonamide, 96% (S)-N-(−)-p-Tolylsulfinyltryptamine, H3C CH3 C24H31NO3S HO CH3 [60933‑63‑3] 97% O H3C CH3 FW 413.57 S C10H17NO3S N [288159‑11‑5] O CH3 FW 231.31 O H C17H18N2OS N H N S 2 O FW 298.40 S H3C CH3 O O N H 41390 376612 588512 (1R)-10‑Camphorsulfonamide, 97%

[72597‑34‑3] H3C CH3 C10H17NO3S FW 231.31 O O S O

NH2

375632

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 69 Sulfonates/Sulfinates (S)-(+)-2‑Methylbutyl methane- (1R)-(−)-10‑Camphorsulfonic acid, (1R,2S,5R)-(−)-Menthyl (S)-p-tolu- sulfonate, 99% 98% enesulfinate, 98%

[104418‑40‑8] [35963‑20‑3] [1517‑82‑4] CH3 O H3C CH3 CH3 H C O S CH SO3H C6H14O3S 3 3 C10H16O4S O C17H26O2S O O FW 166.24 FW 232.30 FW 294.45 S O 303852 282146 H3C H3C CH3

278750 (2R,3R)-Butanediol bis(methane- (1S)-(+)-10‑Camphorsulfonic acid, sulfonate), 97% 99% (1S,2R,5S)-(+)-Menthyl (R)-p-tolu-

C6H14O6S2 O CH3 [3144‑16‑9] enesulfinate, 98% O H3C CH3 FW 246.30 H3C S O O S CH3 C10H16O4S O [91796‑57‑5] CH3 O FW 232.30 O CH3 Organic Building Blocks HO S O C17H26O2S O O 681369 FW 294.45 S O C2107 [(1R)-(endo,anti)]-(+)-3‑Bromocam- H3C H3C CH3 ‑ phor-8 sulfonic acid ammonium (1R)-(−)-10‑Camphorsulfonic acid 278742 salt, 99% ammonium salt ‑ ‑ [14575 84 9] O ‑ ‑ CH3 [82509 30 6] H C CH3 O C H BrO S·NH H4NO S 3 10 15 4 3 H S O NH + O C10H19NO4S 4 O FW 328.22 Br FW 249.33 O H C 3 O 188360 B60002 ‑ ‑ (1S)-(+)-3‑Bromocamphor-10‑sul- (S)-(+)-1 Methylpropyl 4 methyl- fonic acid hydrate, 98% benzenesulfonate, 95% ‑ ‑ [206860‑46‑0] [50896 54 3] O H3C CH3 S O C11H16O3S CH C10H15BrO4S·xH2O H O 3 FW 228.31 CH • xH2O H C 3 FW 311.19 (Anh) O Br 3 HO S O O 536229

374121

Others (R)-(−)-1‑Aminoethylphosphonic (1S)-(+)-(1‑Aminopropyl)phospho- (S)-(−)-Propylene carbonate, 98% acid nic acid, 98% [51260‑39‑0] CH3 [60687‑36‑7] [98048‑99‑8] C4H6O3 H2N O O OO C2H8NO3P POH C3H10NO3P H3C P OH FW 102.09 H3C O FW 125.06 OH FW 139.09 H2N OH A6801 471895 540005

(S)-(+)-1‑Aminoethylphosphonic (R)-(+)-Propylene carbonate, 98% (1R)-(+)-(1‑Amino-2‑methylpropyl) acid, 99% phosphonic acid, 98% ‑ ‑ [16606 55 6] CH 3 ‑ ‑ [66068‑76‑6] C4H6O3 [66254 56 6] CH H2N O OO 3 O C H NO P POH FW 102.09 C4H12NO3P 2 8 3 H C H3C POH 3 OH O FW 125.06 FW 153.12 H2N OH 540013 367559 471860

70 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. (1S)-(−)-(1‑Amino-2‑methylpropyl) (R)-N-(α-Methylbenzyl)hydroxyl- (1R,E)-(+)-Camphorquinone phosphonic acid, 98% amine oxalate salt, ≥96% 3‑oxime, 99%

‑ ‑ ‑ ‑ ‑ ‑ [66254 55 5] CH [118743 81 0] CH O [31571 14 9] H C CH 3 O 3 HO 3 3 C4H12NO3P C8H11NO · C2H2O4 OH • OH C10H15NO2 H3C P OH N HO N H FW 153.12 H2N OH FW 227.21 O FW 181.23 Blocks Building Organic O CH3 471879 690236 273112 (S)-(−)-2‑Hydroxy-N-methylsuccini- (S)-N-(α-Methylbenzyl)hydroxyl- − mide, 97% amine oxalate salt, ≥96.0% (1S)-( )-Camphorsulfonylimine, 99% [104612‑35‑3] OH ‑ ‑ [78798 33 1] CH O OH 3 [60886‑80‑8] C5H7NO3 C8H11NO· C2H2O4 OH • H3C CH3 OO N FW 129.11 N FW 227.21 H O OH C10H15NO2S CH3 FW 213.30

370142 690333 N S O O ‑ (S)-(−)-1,2‑Epithiooctane, 90% (R)-(+)-4-(Methoxymethyl)-1,3 di- 318361 oxolan-2‑one, 98% [244221‑84‑9] CH2(CH2)4CH3 C8H16S (1R)-(+)-Camphorsulfonylimine, [185836‑34‑4] S OCH3 FW 144.28 C5H8O4 OO 99% FW 132.11 477311 O [107869‑45‑4] H3C CH3 C H NO S 474010 [3aS-(3aα,4α,5β,7aα)]-5‑Azido- 10 15 2 FW 213.30 7‑bromo-3a,4,5,7a-tetrahydro- − ‑ N (S)-( )-4-(Methoxymethyl)-1,3 di- 2,2‑dimethyl-1,3‑benzodioxol-4‑ol, S ‑ O O oxolan-2 one, 98% 99% 319716 [135682‑18‑7] OCH [171916‑75‑9] 3 Br C5H8O4 OO C9H12BrN3O3 O (1R)-Camphor oxime, ≥97.0% (GC, FW 132.11 CH3 O FW 290.11 O CH3 N3 sum of enantiomers) 474002 OH [2792‑42‑9] H C CH3 493406 3 (S)-(–)-3‑Acetylthio-2‑methyl- C10H17NO FW 167.25 N propanoic acid, 97% (1R)-(−)-10‑Camphorsulfonyl H3C HO ‑ ‑ chloride, 97% [76497 39 7] O O 21335 C6H10O3S H3C S OH ‑ ‑ [39262 22 1] Cl FW 162.21 CH3 H3C C H ClO S H C O S O 10 15 3 3 (R)-(+)-4-(2‑Chlorophenyl)-2‑hy- 472522 FW 250.74 O droxy-5,5‑dimethyl- 1,3,2‑dioxaphosphorinane 2‑oxide, (R)-(+)-Methyl p-tolyl sulfoxide, 301949 97% 99% (1S)-(+)-10‑Camphorsulfonyl [98674‑87‑4] ‑ ‑ [1519 39 7] O C11H14ClO4P O chloride, 97% O S P C8H10OS CH FW 276.65 HO 3 O Cl FW 154.23 [21286‑54‑4] CH3 H3C H3C CH3 CH3 C10H15ClO3S 343609 FW 250.74 464392 O O S O (S)-(−)-Methyl p-tolyl sulfoxide, Cl (S)-(−)-4-(2‑Chlorophenyl)-2‑hy- 99% 219576 droxy-5,5‑dimethyl- 1,3,2‑dioxaphosphorinane 2‑oxide, [5056‑07‑5] O (1S,E)-(−)-Camphorquinone 3‑ox- 97% C8H10OS S CH3 FW 154.23 ime, 99% H C [98674‑86‑3] 3 Cl ‑ ‑ C11H14ClO4P O [251645 83 7] CH3 O 339997 H3C FW 276.65 P C10H15NO2 CH3 HO CH3 O O FW 181.23 CH3 N OH 464406 273120

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 71 (4R)-2‑Hydroxy-5,5‑dimethyl- (S)-(−)-N-(1‑Phenylethyl)maleimide, (S)-(−)-Aminoglutethimide, 97% 4‑phenyl-1,3,2‑dioxaphosphorinan 97% [57288‑03‑6] 2‑oxide, 98% NH2 [60925‑76‑0] C13H16N2O2 O FW 232.28 [98674‑80‑7] C12H11NO2 O N CH3 O O N O C11H15O4P O FW 201.22 H C H P 3 CH FW 242.21 HO O 3 CH3 545864 461563 448427 (+)-Allylboronic acid pinanediol (S)-(−)-2‑Hydroxy-4-(2‑methoxy- ester, 97% (+)-Chloromethyl isomenthyl ether, phenyl)-5,5‑dimethyl- 97% 1,3,2‑dioxaphosphorinane 2‑oxide, C13H21BO2 H3C CH3 FW 220.12 97% H CH3 [144177‑48‑0] O CH3 CH2 B C11H21ClO CH3 [98674‑83‑0] H O FW 204.74 CH3 H3C O Cl C12H17O5P H3C 694584 FW 272.23 O O OCH3 453692 P O OH (4S)-4-[(1R)-2‑Azido-1-(benzyloxy) (+)-Chloromethyl menthyl ether, 464384 ethyl]-2,2‑dimethyl-1,3‑dioxolane 97% C14H19N3O3 (R)-(+)-2‑Hydroxy-4-(2‑methoxy- N3 [103128‑76‑3] FW 277.32 CH3 ‑ phenyl)-5,5 dimethyl- O C11H21ClO H3C 1,3,2‑dioxaphosphorinane 2‑oxide, OO FW 204.74 CH3 O Cl 97% H3C CH3

349925 [98674‑82‑9] 573213 H3CO

C12H17O5P HO O (−)-Chloromethyl menthyl ether, FW 272.23 O P (2R,5S)-5‑Methyl-4,4‑diphenyl- O CH3 ‑ 97% CH3 1,3,2 dioxathiolane, 98%

‑ ‑ 464376 [126577‑49‑9] [26127 08 2] CH H C Ph 3 3 Ph C15H14O3S C11H21ClO H C 3 O O FW 204.74 − ‑ FW 274.33 S CH O Cl (S)-( )-1,2 Epithiododecane 3 O [308103‑61‑9] 349917 CH2(CH2)8CH3 366714 C12H24S S FW 200.38 (R)-(+)-N-(1‑Phenylethyl)male- (1R)-(−)-Nopol benzyl ether, 95% imide, 97% 477346 [74851‑17‑5] H3C CH3 ‑ ‑ [6129 15 3] (R)-(+)-Aminoglutethimide, 97% C18H24O C12H11NO2 O N O FW 256.38 ‑ ‑ O FW 201.22 [55511 44 9] NH H3C 2 C13H16N2O2

FW 232.28 CH3 340375 461555 O N O H

545872

72 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis. PTS—New Amphiphile for Metathesis and Cross-Coupling in Water

Recently introduced by Professor Bruce Lipshutz of UC, Lipophilic substrates and catalysts can efficiently enter Santa Barbara, polyoxyethanyl α-tocopheryl sebacate (PTS) micelles formed by PTS in water, leading to cross-coupling is a nonionic amphiphile that is proving to be a versatile reactions at room temperature without the need for a “solubilizer” for organic molecules in water.1 co-solvent.2

R1 R2

R1 Grubbs II cat . R2 . Grubbs II cat

PTS X 2 Ar R Pd cat ArX + RB(OH). X Pd cat Ar Pd cat. . X-Phos R R Ar Ar R R

O O O O H 4 n O O

PTS (n = ca. 13)

α Polyoxyethanyl -tocopheryl sebacate, 15 wt. % in H2O 698717 10 mL $47.50

References: (1) Sold under license from Zymes, LLC. (2) (a) Lipshutz, B. H. et al. Org. Lett. 2008, 10, 1325. (b) Lipshutz, B. H. et al. Adv. Synth. Catal. 2008, 350, 953. (c) Lipshutz, B. H. et al. Org. Lett. 2008, 10, 1333. (d) Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329. (e) Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta 2008, 41, in press. (f) Lipshutz, B. H. et al. Org. Lett. 2008, 10, ASAP.

sigma-aldrich.com

misc.indd 3 6/18/2009 8:24:09 AM $

Risk & Safety Phrases COMBINATION OF PARTICULAR RISKS: 14/15: Reacts violently with water, liberating extremely flammable gases Risk Phrases 15/29: Contact with water liberates toxic, extremely flammable gas 20/21: Harmful by inhalation and in contact with skin INDICATION OF PARTICULAR RISKS: 20/21/22: Harmful by inhalation, in contact with skin and if swallowed R1: Explosive when dry 20/22: Harmful by inhalation and if swallowed 2: Risk of explosion by shock, friction, fire or other sources of 21/22: Harmful in contact with skin and if swallowed ignition 23/24: Toxic by inhalation and in contact with skin 3: Extreme risk of explosion by shock, friction, fire or other 23/24/25: Toxic by inhalation, in contact with skin and if swallowed sources of ignition 23/25: Toxic by inhalation and if swallowed 4: Forms very sensitive explosive metallic compounds 24/25: Toxic in contact with skin and if swallowed 5: Heating may cause an explosion 26/27: Very toxic by inhalation and in contact with skin 6: Explosive with or without contact with air 26/27/28: Very toxic by inhalation, in contact with skin and if 7: May cause fire swallowed 8: Contact with combustible material may cause fire Risk and Safety 26/28: Very toxic by inhalation and if swallowed 9: Explosive when mixed with combustible material 27/28: Very toxic in contact with skin and if swallowed 10: Flammable 36/37: Irritating to eyes and respiratory system 11: Highly flammable 36/37/38: Irritating to eyes, respiratory system and skin 12: Extremely flammable 36/38: Irritating to eyes and skin 14: Reacts violently with water 37/38: Irritating to respiratory system and skin 15: Contact with water liberates extremely flammable gases 39/23: Toxic: danger of very serious irreversible effects through 16: Explosive when mixed with oxidizing substances inhalation 17: Spontaneously flammable in air 39/23/24: Toxic: danger of very serious irreversible effects through 18: In use may form flammable/explosive vapor-air mixture inhalation and in contact with skin 19: May form explosive peroxides 39/23/24/25: Toxic: danger of very serious irreversible effects through 20: Harmful by inhalation inhalation, in contact with skin and if swallowed 21: Harmful in contact with skin 39/23/25: Toxic: danger of very serious irreversible effects through 22: Harmful if swallowed inhalation and if swallowed 23: Toxic by inhalation 39/24: Toxic: danger of very serious irreversible effects in contact 24: Toxic in contact with skin with skin 25: Toxic if swallowed 39/24/25: Toxic: danger of very serious irreversible effects in contact 26: Very toxic by inhalation with skin and if swallowed 27: Very toxic in contact with skin 39/25: Toxic: danger of very serious irreversible effects if swallowed 28: Very toxic if swallowed 39/26: Very toxic: danger of very serious irreversible effects through 29: Contact with water liberates toxic gas inhalation 30: Can become highly flammable in use 39/26/27: Very toxic: danger of very serious irreversible effects through inhalation and in contact with skin 31: Contact with acids liberates toxic gas 39/26/27/28: Very toxic: danger of very serious irreversible effects through 32: Contact with acids liberates very toxic gas inhalation, in contact with skin and if swallowed 33: Danger of cumulative effects 39/26/28: Very toxic: danger of very serious irreversible effects through 34: Causes burns inhalation and if swallowed 35: Causes severe burns 39/27: Very toxic: danger of very serious irreversible effects in contact 36: Irritating to the eyes with skin 37: Irritating to the respiratory system 39/27/28: Very toxic: danger of very serious irreversible effects in 38: Irritating to the skin contact with skin and if swallowed 39: Danger of very serious irreversible effects 39/28: Very toxic: danger of very serious irreversible effects if 40: Limited evidence of a carcinogenic effect swallowed 41: Risk of serious damage to eyes 42/43: May cause sensitization by inhalation and skin contact 42: May cause sensitization by inhalation 48/20: Harmful: danger of serious damage to health by prolonged 43: May cause sensitization by skin contact exposure through inhalation 44: Risk of explosion if heated under confinement 48/20/21: Harmful: danger of serious damage to health by prolonged 45: May cause cancer exposure through inhalation and in contact with skin 46: May cause heritable genetic damage 48/20/21/22: Harmful: danger of serious damage to health by prolonged 48: Danger of serious damage to health by prolonged exposure exposure through inhalation, in contact with skin and if 49: May cause cancer by inhalation swallowed 50: Very toxic to aquatic organisms 48/20/22: Harmful: danger of serious damage to health by prolonged 51: Toxic to aquatic organisms exposure through inhalation and if swallowed 52: Harmful to aquatic organisms 48/21: Harmful: danger of serious damage to health by prolonged 53: May cause long-term adverse effects in the aquatic exposure in contact with skin environment 48/21/22: Harmful: danger of serious damage to health by prolonged 54: Toxic to flora exposure in contact with skin and if swallowed 55: Toxic to fauna 48/22: Harmful: danger of serious damage to health by prolonged 56: Toxic to soil organisms exposure if swallowed 57: Toxic to bees 48/23: Toxic: danger of serious damage to health by prolonged 58: May cause long-term adverse effects in the environment exposure through inhalation 59: Dangerous for the ozone layer 48/23/24: Toxic: danger of serious damage to health by prolonged 60: May impair fertility exposure through inhalation and in contact with skin 61: May cause harm to the unborn child 48/23/24/25: Toxic: danger of serious damage to health by prolonged 62: Possible risk of impaired fertility exposure through inhalation, in contact with skin and if 63: Possible risk of harm to the unborn child swallowed 64: May cause harm to breast-fed babies 48/23/25: Toxic: danger of serious damage to health by prolonged exposure through inhalation and if swallowed 65: Harmful: may cause lung damage if swallowed 48/24: Toxic: danger of serious damage to health by prolonged 66: Repeated exposure may cause skin dryness or cracking exposure in contact with skin 67: Vapors may cause drowsiness and dizziness 48/24/25: Toxic: danger of serious damage to health by prolonged 68: Possible risk of irreversible effects exposure in contact with skin and if swallowed

74 sigma-aldrich.com TO ORDER: Contact your local Sigma-Aldrich office (see back cover), or visit sigma-aldrich.com/chemicalsynthesis.

70978 ChemFiles 9.3 Inside Pages.indd 8 6/4/2009 1:06:05 PM $

48/25: Toxic: danger of serious damage to health by prolonged 42: During fumigation/spraying wear suitable respiratory exposure if swallowed equipment (appropriate wording to be specified by the 50/53: Very toxic to aquatic organisms, may cause long-term adverse manufacturer) effects in the aquatic environment 43: In case of fire, use ... (indicate in the space the precise type of 51/53: Toxic to aquatic organisms, may cause long-term adverse fire-fighting equipment. If water increases the risk add - Never effects in the aquatic environment use water) 52/53: Harmful to aquatic organisms, may cause long-term adverse 45: In case of accident or if you feel unwell, seek medical advice effects in the aquatic environment immediately (show label where possible) Risk and Safety 68/20: Harmful: possible risk of irreversible effects through inhalation 46: If swallowed, seek medical advice immediately and show this 68/20/21: Harmful: possible risk of irreversible effects through inhalation container or label and in contact with skin 47: Keep at temperature not exceeding ... ºC (to be specified by 68/20/21/22: Harmful: possible risk of irreversible effects through inhalation, the manufacturer) in contact with skin and if swallowed 48: Keep wet with ... (appropriate material to be specified by the 68/20/22: Harmful: possible risk of irreversible effects through inhalation manufacturer) and if swallowed 49: Keep only in the original container 68/22: Harmful: possible risk of irreversible effects if swallowed 50: Do not mix with ... (to be specified by the manufacturer) 68/21: Harmful: possible risk of irreversible effects in contact with 51: Use only in well-ventilated areas skin 52: Not recommended for interior use on large surface areas 68/21/22: Harmful: possible risk of irreversible effects in contact with 53: Avoid exposure - obtain special instruction before use skin and if swallowed 56: Dispose of this material and its container to hazardous or special waste collection point Safety Phrases 57: Use appropriate container to avoid environ mental contamination INDICATION OF SAFETY PRECAUTIONS: 59: Refer to manufacturer/supplier for information on recovery/ S1: Keep locked up recycling 2: Keep out of the reach of children 60: This material and/or its container must be disposed of as 3: Keep in a cool place hazardous waste 4: Keep away from living quarters 61: Avoid release to the environment. Refer to special instructions/ 5: Keep contents under ... (appropriate liquid to be specified safety data sheet by the manufacturer) 62: If swallowed, do not induce vomiting: seek medical advice 6: Keep under ... (inert gas to be specified by the manufacturer) immediately and show this container or label 7: Keep container tightly closed 63: In case of accident by inhalation, remove casualty to fresh air 8: Keep container dry and keep at rest 9: Keep container in a well-ventilated place 64: If swallowed, rinse mouth with water (only if the person is 12: Do not keep the container sealed conscious) 13: Keep away from food, drink and animal feeding stuffs COMBINATION OF SAFETY PRECAUTIONS: 14: Keep away from ... (incompatible materials to be indicated by the manufacturer) 1/2: Keep locked up and out of the reach of children 15: Keep away from heat 3/7: Keep container tightly closed in a cool place 16: Keep away from sources of ignition - No smoking 3/9/14: Keep in a cool well-ventilated place away from ... (incompatible materials to be indicated by manufacturer) 17: Keep away from combustible material 3/9/14/49: Keep only in the original container in a cool well-ventilated 18: Handle and open container with care place away from ... (incompatible materials to be indicated by 20: When using, do not eat or drink manufacturer) 21: When using, do not smoke 3/9/49: Keep only in the original container in a cool well-ventilated 22: Do not breathe dust place 23: Do not breathe gas/fumes/vapor/spray (appropriate wording 3/14: Keep in a cool place away from ... (incompatible materials to to be specified by the manufacturer) be indicated by the manufacturer) 24: Avoid contact with skin 7/8: Keep container tightly closed and dry 25: Avoid contact with eyes 7/9: Keep container tightly closed and in a well-ventilated place 26: In case of contact with eyes, rinse immediately with plenty 7/47: Keep container tightly closed and at a temperature not of water and seek medical advice exceeding ... ºC (to be specified by manufacturer) 27: Take off immediately all contaminated clothing 20/21: When using, do not eat, drink or smoke 28: After contact with skin, wash immediately with plenty of ... 24/25: Avoid contact with skin and eyes (to be specified by the manufacturer) 27/28: After contact with skin, take off immediately all contaminated 29: Do not empty into drains clothing and wash immediately with plenty of ... (to be 30: Never add water to this product specified by the manufacturer) 33: Take precautionary measures against static discharges 29/35: Do not empty into drains, dispose of this material and its 35: This material and its container must be disposed of in a safe container in a safe way way 29/56: Do not empty into drains, dispose of this material and its 36: Wear suitable protective clothing container at hazardous or special waste-collection point 37: Wear suitable gloves 36/37: Wear suitable protective clothing and gloves 38: In case of insufficient ventilation, wear suitable respiratory 36/37/39: Wear suitable protective clothing, gloves and eye/face equipment protection 39: Wear eye/face protection 36/39: Wear suitable protective clothing and eye/face protection 40: To clean the floor and all objects contaminated by this 37/39: Wear suitable gloves and eye/face protection material use ... (to be specified by the manufacturer) 47/49: Keep only in the original container at temperature not 41: In case of fire and/or explosion do not breathe fumes exceeding ... ºC (to be specified by manufacturer) Pictograms Pictograms are based on widely accepted standards.

G H J F K T L Xn M I Q R E O F+ T+ Xi C B N R Explosive Oxidizing Highly Flammable Toxic or Harmful or Corrosive Biohazard Dangerous for the Radioactive or Extremely Very Toxic Irritant Environment Flammable

Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 75

70978 ChemFiles 9.3 Inside Pages.indd 9 6/4/2009 1:06:05 PM Cat. No. Risk Safety Cat. No. Risk Safety

00031 Xi: 36/37/38 ...... 26 211354 Xi: 36/37/38 ...... 26-36 00696 Xi: 36/37/38-43 ...... 26-36/37 218235 ...... 23-24/25 00791 Xn: 22-37/38-41 ...... 26-39 218243 ...... 23-24/25 00846 ...... 23-24/25 218294 Xi: 36/37/38 ...... 26 00851 T: 23/24/25 ...... 36/37/39-45 218359 Xi: 36/37/38 ...... 26-36 00873 Xn: 20/21/22-36/37/38 ...... 26-36 218367 Xi,N: 10-38-43-50/53 ...... 24-37-60-61 02300 Xi: 37/38-41 ...... 26-36 218391 Xi: 36/37/38 ...... 26-36 04855 T: 45-20/21-37/38-41-43-52/53-68 ...... 53-26-36/37/39-45-61 219576 C: 34 ...... 26-36/37/39-45 05023 C: 22-34 ...... 26-36/37/39-45 21987 10 ...... 23-24/25 06368 Xn: 22-36/37/38 ...... 26 21989 10 ...... 23-24/25 06674 Xn: 22-37/38-41 ...... 26-39 220442 Xn: 36/37/38-42/43 ...... 23-26-36/37

Risk & Safety 06782 Xn: 22 ...... 220566 Xn: 36/37/38-42 ...... 23-26-36 07858 Xn: 22-36/37/38 ...... 26 220574 Xn: 36/37/38-42 ...... 23-26-36 08011 F: 11 ...... 16 22110 Xi: 36/37/38 ...... 26-36 08601 Xi: 37/38-41 ...... 26-39 224464 Xi: 37/38-41 ...... 26-39 09222 C: 22-34 ...... 26-36/37/39-45 226173 C: 34 ...... 26-36/37/39-45 09267 C: 22-34 ...... 26-36/37/39-45 227803 ...... 23-24/25 112577 Xi: 36/37/38 ...... 26-36 230340 Xi: 10-36/37 ...... 24 115541 C: 21/22-34 ...... 26-28-36/37/39-45 232386 10 ...... 115568 C: 21/22-34 ...... 26-28-36/37/39-45 233935 Xi: 36/37/38 ...... 26-36 11558 Xn: 22-36/37/38 ...... 26 235180 Xi: 37/38-41 ...... 26-36 11584 Xn: 22-36/37/38 ...... 26 236691 Xi: 10-36/37-67 ...... 9-13-24/25-26-46 12348 Xi: 36/37/38 ...... 26-36 237442 Xi: 36/37/38 ...... 26-36 12351 Xi: 36/37/38 ...... 26-36 237450 Xi: 36/37/38 ...... 26-36 124931 22 ...... 36 237612 Xi: 36/37/38 ...... 26-36 132527 C: 22-34-37 ...... 26-36/37/39-45 237620 Xi: 36/37/38 ...... 26-36 13597 Xi: 36/37/38 ...... 26-36 237698 Xi: 10-36/37-67 ...... 9-13-24-25-26-46 13732 ...... 22-24/25 237744 ...... 23-24/25 139114 F,Xi: 11-43 ...... 16-36/37 238856 C: 34 ...... 23-26-36-45 141879 T: 23/25 ...... 36/37/39-45 238864 C: 34 ...... 23-26-36-45 147982 Xi: 36/37/38 ...... 26-36 241407 F,C: 11-20/21/22-34 ...... 16-26-36/37/39-45 147990 Xi: 36/37/38 ...... 26-36 241806 ...... 23-24/25 15022 Xi: 36/37/38 ...... 26-36 242063 Xn: 22-36 ...... 26 154210 ...... 22-24/25 242071 Xi: 36/37/38 ...... 26-36 155268 Xi: 36/37/38 ...... 26-36 243159 Xi: 36/37/38 ...... 26-36/37 155616 Xi: 36/37/38 ...... 26-36 243167 ...... 23-24/25 156868 Xi: 36/37/38 ...... 26-36 243175 ...... 22-24/25 163449 Xi: 36 ...... 26-36 245305 T,N: 23-34-51/53 ...... 26-36/37/39-45-61 16571 Xi: 36/37/38 ...... 26-36 245526 C: 34 ...... 26-36/37/39-45 16749 Xn: 22 ...... 247030 Xn: 10-36-48/22 ...... 23-26-36 16995 Xi: 36/37/38 ...... 23-26-36 247065 Xi: 36/37/38 ...... 26-36 17241 Xi: 36/37/38 ...... 26-36 247308 Xn: 10-20/21/22 ...... 16-36 18069 C: 34 ...... 26-28-36/37/39-45 248509 Xn: 40-52 ...... 23-24/25-36/37 18072 C: 34 ...... 26-28-36/37/39-45 248886 Xi: 36/37/38 ...... 26-36 180807 Xi: 36/37/38 ...... 26-36/37/39 248967 Xi: 36/37/38 ...... 26-36 18159 C: 34 ...... 26-36/37/39-45 248983 Xi: 36/37/38 ...... 26-36 18165 C: 22-34 ...... 26-36/37/39-45 249246 ...... 23-24/25 18196 C: 34 ...... 26-36/37/39-45 249262 ...... 22-24/25 18241 F,C: 11-22-34 ...... 26-36/37/39-45 250023 Xi: 10-36/37/38 ...... 26-36 18509 Xi: 36/38 ...... 26 25112 C: 34 ...... 26-36/37/39-45 186511 Xi: 36/37/38 ...... 26-36 25113 C: 34 ...... 26-36/37/39-45 186546 Xi: 36/37/38 ...... 26-36 251542 ...... 22-24/25 186708 Xi: 36 ...... 26 251550 ...... 22-24/25 187658 ...... 23-24/25 252840 Xi: 36/38 ...... 26-36 188417 ...... 23-24/25 25301 Xi: 36/37/38 ...... 26-36/37/39 189006 Xi: 36/37/38 ...... 26-36 253022 ...... 22-24/25 190047 Xn: 21/22 ...... 24/25 253030 ...... 22-24/25 190438 C: 34 ...... 26-36/37/39-45 254606 ...... 23-24/25 19159 Xi: 36/37/38 ...... 26-36 254827 ...... 22-24/25 19162 Xi: 36/37/38 ...... 26 256269 ...... 22-24/25 19163 Xi: 36/37/38 ...... 26-36 256277 ...... 22-24/25 192384 Xi: 36/37/38 ...... 26-37/39 256285 Xi: 36/37/38 ...... 26-36 19377 F: 11 ...... 16 256293 Xi: 36/37/38 ...... 26-36 194107 ...... 23-24/25 256323 Xn: 22 ...... 23-24/25 19506 T: 25-37/38-41 ...... 26-39-45 256331 Xn: 22 ...... 23-24/25 195936 Xi: 36/37/38 ...... 26-36 263907 ...... 22-24/25 196436 10 ...... 23-24/25 267872 ...... 22-24/25 19929 Xn: 22-36/37/38 ...... 26 268070 Xi: 10-36/37/38 ...... 26-36 20260 ...... 22-24/25 270148 10 ...... 16 211346 Xi: 36/37/38 ...... 26-36 273112 ...... 22-24/25

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273120 Xi: 22-43 ...... 36/37 309710 Xi: 36/37/38 ...... 26-36 27477 10 ...... 23-24/25 309753 Xi: 36/37/38 ...... 26-36 276065 ...... 22-24/25 310425 10 ...... 16-29-33 276073 ...... 22-24/25 310476 Xi: 36/37/38 ...... 26-36

27618 10 ...... 23-24/25 316520 Xi: 36/37/38 ...... 26-36 Safety & Risk 276286 Xn: 22-43 ...... 36/37 316598 Xi: 36 ...... 26 277037 Xi: 36/37/38 ...... 26-36 317322 ...... 22-24/25 277061 Xi: 36/37/38 ...... 26-36 318035 Xi: 36/37/38 ...... 26-36 277754 Xi: 10-36/37/38 ...... 26-36 318361 Xi: 36/37/38 ...... 26-36 277762 Xi: 10-36/37 ...... 24 319716 Xi: 36/37/38 ...... 26-36 278807 T+: 26/27/28 ...... 22-36/37/39-45 323128 Xn: 22-36/37/38 ...... 26-36 279676 F,Xi: 11-36/37/38 ...... 16-26 323144 ...... 22-24/25 279870 Xn: 22 ...... 23-36 324612 Xi: 36/37/38 ...... 26-37/39 279889 Xn: 22 ...... 23-36 324922 Xi: 36/37/38 ...... 26-36 279897 Xi: 36/37/38 ...... 26-36 325058 Xi: 36/37/38 ...... 26-36 279900 Xi: 36/37/38-43 ...... 26-36 325066 Xi: 36/37/38 ...... 26-36 281573 ...... 23-24/25 325090 Xi: 36/37/38 ...... 26-36 281581 Xi: 36/37/38 ...... 26-36 327131 Xi: 10-36/37/38 ...... 16-26-36 281697 Xi: 36/37/38 ...... 26-36 327247 Xi: 36/37/38 ...... 26-36 282146 C: 34 ...... 26-36/37/39-45 328243 Xi: 36/37/38 ...... 26-36 28255 Xn: 22 ...... 26-36 328413 Xn: 22-36/37/38 ...... 26-36 283118 T: 23/24/25-36/37/38-42/43 ...... 23-26-36/37/39-45 328847 Xn: 22 ...... 284483 Xi: 36/37/38 ...... 26-36/37 329142 Xi: 36/37/38 ...... 26-36 284491 C: 34 ...... 26-36/37/39-45 329177 Xi: 36/37/38 ...... 26-37/39 284785 Xn: 22 ...... 36/37 329487 Xi: 36/37/38 ...... 26-36 287784 ...... 22-24/25 329967 Xn: 22 ...... 36 287792 Xi: 36/37/38 ...... 26 330515 Xi: 10-36/37/38 ...... 16-26 28964 T: 25-36/37/38 ...... 26-36/37/39-45 330523 Xn: 10-20 ...... 24/25 289981 ...... 22-24/25 331074 Xi: 36/37/38 ...... 26-36 29177 C: 10-20/21/22-34-40 ...... 26-36/37/39-45 331813 Xi: 36/37/38 ...... 26-37/39 292176 Xi: 36/37/38 ...... 26-36 331848 Xi: 36/37/38 ...... 26-37/39 29438 T: 45-20/21-37/38-41-43-52/53-68 ...... 53-26-36/37/39-45-61 331856 Xi: 36/37/38 ...... 26-37/39 295957 Xn: 36/37/38-42/43 ...... 23-26-36/37 331872 Xi: 36/37/38 ...... 26-37/39 296643 F,C,N: 11-20/22-35-50 ...... 16-26-28- 331880 Xi: 36/37/38 ...... 26-36 36/37/39-45-61 331899 Xi: 36/37/38 ...... 26-36 296651 F,C,N: 11-20/22-35-50 ...... 9-16-26-28- 334235 Xi: 36/37/38 ...... 26-36/37/39 36/37/39-45-61 335975 F,Xi: 11-36-66-67 ...... 16-26 296678 ...... 23-24/25 33622 Xi: 36 ...... 26-36 296686 Xi: 36/37/38 ...... 26 336505 C: 10-21/22-34 ...... 26-36/37/39-45 296708 Xn: 10-20/21/22-36 ...... 16-26-27-36/37/39-45 336513 C: 10-34 ...... 16-26-36/37/39-45 296902 Xi: 36/37/38 ...... 26-36 337412 Xi: 36/37/38 ...... 26-36 296910 Xi: 36/37/38 ...... 26-36 337420 Xi: 36/37/38 ...... 26-36 297658 Xi: 36/37/38 ...... 26-36 338125 Xn: 22-36/37/38-42/43 ...... 23-36/37-45 297682 C: 34 ...... 26-36/37/39-45 338419 Xi: 36/37/38 ...... 26-36 298336 Xi: 36/37/38 ...... 26-36 338710 F,Xi: 11-36-66-67 ...... 9-16-26 298344 Xi: 36/37/38 ...... 26-36/37/39 339814 Xi: 36/37/38 ...... 26-37/39 300438 Xi: 36/37/38 ...... 26-36 339822 Xi: 36/37/38 ...... 26-37/39 300446 Xi: 36/37/38 ...... 26-36 340235 Xn: 20/21/22-36/37/38 ...... 26-36 300489 Xi: 36/37/38 ...... 26-36 340243 Xi: 36/37/38 ...... 26-36 300500 Xi: 36/37/38 ...... 26-36 340308 10 ...... 300535 Xi: 36/37/38 ...... 26-37/39 340332 Xi: 36/37/38 ...... 26-36/37/39 301469 Xi: 36/37/38 ...... 26-36 340367 Xn: 22-36/37/38 ...... 26-37/39 30169 Xi: 36/37/38 ...... 26 340375 Xi: 36/37/38 ...... 26-37/39 30192 C: 34 ...... 26-36/37/39-45 340499 Xn: 21-38 ...... 26-36 301949 C: 34 ...... 26-36/37/39-45 341363 Xi: 36/37/38 ...... 26-36 302147 Xn: 20/21/22-36/37/38 ...... 26-36 343544 ...... 23-24/25 302775 Xn: 20/21/22-36/37/38 ...... 26-36 343609 ...... 22-24/25 302945 ...... 23-24/25 343641 Xi: 36/37/38 ...... 26-36 303461 Xi: 36/37/38 ...... 26-36 345482 ...... 23-24/25 303488 Xi: 36/37/38 ...... 26-36 345598 Xi: 36/37/38 ...... 26-37/39 305251 T: 25 ...... 36-45 345628 Xi: 36/37/38 ...... 26-37/39 305715 Xi,N: 10-36/37/38-43-50 ...... 26-36/37-61 345849 Xi: 36 ...... 26 305758 Xi: 36/37/38 ...... 26-37/39 346217 ...... 22-24/25 305766 Xi: 36/37/38 ...... 26-36/37/39 346713 C: 34 ...... 26-36/37/39-45 305790 Xi: 36/37/38 ...... 26-36 346721 C: 34 ...... 26-36/37/39-45 306355 ...... 22-24/25 346810 ...... 23-24/25 306428 Xi: 36/37/38 ...... 26-36 346969 ...... 23-24/25 306797 C: 21/22-35 ...... 23-26-28-36/37/39-45 348368 Xi: 36/37/38 ...... 26-37/39 306800 C: 22-35 ...... 23-26-28-36-45 348562 C: 34 ...... 26-27-36/37/39-45 307084 C: 22-34-37 ...... 26-36/37/39-45 348902 ...... 23-24/25

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348910 ...... 22-24/25 399701 Xn: 20/21/22 ...... 27-36/37/39-45 349607 Xi: 36/37/38 ...... 26-36 399728 Xi: 36/37/38 ...... 26-36 349917 Xi: 36/37/38 ...... 26-36 399736 Xi: 36/37/38 ...... 26-36 349925 Xi: 36/37/38 ...... 26-36 400149 ...... 22-24/25 358924 Xi: 36/37/38 ...... 26-36 401358 C: 20/21/22-34 ...... 26-36-45 359068 ...... 23-24/25 402753 Xn,N: 10-20/21/22-36/37/38-43-51-65 ...... 16-26-36/37-46-61-62 359939 Xi: 36/37/38 ...... 26-36 405086 Xi: 36/37/38 ...... 26-36 361887 Xi: 36/37/38 ...... 26-37/39 405248 C: 20/21/22-34 ...... 16-26-27-36/37/39-45 36323 Xi: 36/37/38 ...... 26 405256 C: 20/21/22-34 ...... 16-26-27-36/37/39-45 363529 Xi: 36/37/38 ...... 26-36 40577 Xn: 22-36/38 ...... 26 363537 Xi: 36/37/38 ...... 26-36 407453 T: 25 ...... 36/37-45

Risk & Safety 363561 ...... 23-24/25 40767 Xi: 36/37/38 ...... 26-36 364002 Xi: 36/37/38 ...... 26-36 408697 Xn: 21-37/38-41 ...... 26-36/37/39 364010 Xi: 36/37/38 ...... 26-36 409650 Xi: 36/37/38 ...... 26-36 364428 Xi: 38 ...... 409731 Xn: 20/21/22-36/37/38 ...... 26-36 364541 Xi: 36/37/38 ...... 26-37/39 410462 Xi: 36/37/38 ...... 26-37/39 364568 Xi: 36/37/38 ...... 26-36 410918 Xi: 36/37/38 ...... 26-36 364886 ...... 22-24/25 411132 Xi: 36/37/38 ...... 26-36 364908 ...... 22-24/25 411140 Xi: 36/37/38 ...... 26-36 366358 Xi: 36/37/38 ...... 26-36 412554 Xi: 36/37/38 ...... 26-36 366366 Xi: 36/37/38 ...... 26-36 412562 Xi: 36/37/38 ...... 26-36 366714 Xi: 36/37/38 ...... 26-37/39 412937 Xi: 10-36/37/38 ...... 16-26-36/37/39 366935 Xi: 36/37/38 ...... 26-37/39 412945 Xi: 10-36/37/38 ...... 16-26-36/37/39 366943 Xi: 36/37/38 ...... 26-37/39 41304 Xn: 22-37/38-41 ...... 26-39 367044 Xi: 36/37/38 ...... 26-37/39 41390 Xi: 36/37/38 ...... 26-36 367435 Xi: 36/37/38 ...... 26-36 415596 Xi: 36/37/38 ...... 26-36 367559 Xi: 36/37/38 ...... 26-37/39 415618 Xi: 36/37/38 ...... 26-36 369675 C: 34 ...... 26-27-36/37/39-45 41566 F,C: 11-22-34 ...... 26-36/37/39-45 370126 Xn: 20/21/22-36/37/38 ...... 26-36 415715 Xi: 36/37/38 ...... 26-38 370142 Xi: 36/37/38 ...... 26-36 415723 Xi: 36/37/38 ...... 26-36 37034 Xi: 36/37/38 ...... 26-36 41609 Xn: 10-21/22-36/37/38-40 ...... 26-36/37 371416 ...... 22-24/25 416932 Xn: 20/21/22-36/37/38 ...... 26-36 372315 ...... 22-24/25 416940 Xn: 20/21/22 ...... 36 373753 Xi: 36/37/38 ...... 26-36 419990 F,N: 11-51/53 ...... 16-61 374113 Xi: 36/37/38 ...... 26-37/39 420018 ...... 22-24/25 374121 C: 34 ...... 26-36/37/39-45 420026 ...... 22-24/25 374636 C: 34 ...... 26-36/37/39-45 420077 Xi: 36/37/38 ...... 26-36 374709 ...... 23-24/25 420131 ...... 23-24/25 375845 Xi,N: 36-43-51/53 ...... 24-26-37-61 420247 F: 11 ...... 376361 Xi,N: 36/37/38-51/53 ...... 26-28-61 420964 Xi: 36/37/38 ...... 26-36 376388 Xn: 22 ...... 23-24/25 421588 Xi: 36/37/38 ...... 26-36 376418 ...... 22-24/25 421650 Xi: 36/37/38 ...... 26-36 376906 ...... 22-24/25 421693 Xi: 36/37/38 ...... 26-36 377392 Xi: 36/37/38 ...... 26-37/39 421731 Xi: 36/37/38 ...... 26-36 377716 Xi: 36/37/38 ...... 26-37/39 421804 Xi: 36/37-41 ...... 26-39 378712 T: 23-34 ...... 26-36/37/39-45 422797 Xi: 36/37/38 ...... 26-36 379093 Xi: 36/37/38 ...... 26-36 422800 Xi: 36/37/38 ...... 26-36 380148 ...... 22-24/25 422886 Xi: 10-36/37/38 ...... 16-26-36 380342 ...... 22-24/25 427470 Xi: 36/37/38 ...... 26-36 382094 ...... 23-24/25 429791 Xi: 36/37/38 ...... 26-36 382175 ...... 22-24/25 429805 Xn: 20/21/22-36/37/38 ...... 23-26-36 382442 ...... 23-24/25 430722 Xi: 36/37/38 ...... 26-36 382981 Xi: 36/37/38 ...... 26-37/39 431737 Xi: 36/37/38 ...... 26-36 384313 ...... 22-24/25 432261 Xi: 36/37/38 ...... 26-36 385514 C: 22-34 ...... 26-36/37/39-45 432628 Xi: 36/37/38 ...... 26-36 388114 Xi: 36/37/38 ...... 26-36 433721 Xi: 36/37/38 ...... 26-36 391190 Xi: 36/37/38 ...... 26-36 433810 Xi: 36/37/38 ...... 26-36/37 391654 Xi: 36/37/38 ...... 26-36 434639 Xn: 22-36/37/38 ...... 26-36 391662 Xi: 36/37/38 ...... 26 436976 ...... 22-24/25 391913 Xi: 36/37/38 ...... 26-37/39 436984 Xi: 41 ...... 26-39 391921 Xi: 36/37/38 ...... 26-37/39 437026 ...... 22-24/25 392308 Xi: 36/37/38 ...... 26-36 438979 ...... 22-24/25 392480 T+: 26/27/28 ...... 28-36/37-45 439053 Xn: 22-36/37/38 ...... 26-36/37/39 39277 Xi: 36/37/38 ...... 26-36/37 439061 Xn: 22-36/37/38 ...... 26-36/37/39 393967 Xn: 20/21/22 ...... 27-36/37/39-45 43948 Xn: 22-36 ...... 26-36 394009 C: 20/21/22-34 ...... 26-36/37/39-45 440329 Xi: 36/37/38 ...... 26-36 396729 Xn: 22-36/37/38 ...... 26-36 440833 Xi: 36/37/38 ...... 26-36 397164 F: 11-36/37/38 ...... 16-26-36/37/39 440841 Xi: 36/37/38 ...... 26-36 397172 F,Xi: 11-36/37/38 ...... 16-26 441015 ...... 22-24/25 39867 Xn: 22-37/38-41 ...... 26-39 441279 Xn: 22-41-43 ...... 24-26-37/39

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441287 Xi: 36/37/38 ...... 26-36 464384 Xi: 36/37/38 ...... 26-36 441570 Xi: 36/37/38 ...... 26-36 464392 Xi: 36/37/38 ...... 26-36 441619 Xi,N: 10-50/53 ...... 36/37-60-61 464406 Xi: 36/37/38 ...... 26-36 444537 Xi: 36/37/38 ...... 26-36 464821 T+: 10-26/28-36/37/38-40-41-43 ...... 16-24-26-36/37/39-45

445347 Xi: 36/37/38 ...... 26-36 465054 Xi: 36/37/38 ...... 26-36 Safety & Risk 445355 Xi: 36/37/38 ...... 26-36 465062 N: 51/53 ...... 61 445584 Xi: 36/37/38 ...... 26-36 468347 C: 20/21/22-34 ...... 26-27-28-36/37/39-45 445940 Xi: 36/37/38 ...... 26-36 469424 Xi: 36/37/38 ...... 26-36 445959 Xi: 36/37/38 ...... 26-36 469432 Xi: 36/37/38 ...... 26-36 446351 Xi: 36/38 ...... 26-36 469653 T: 23/24/25-36/37/38-41 ...... 22-26-36/37/39-45 447056 C: 34 ...... 26-36/37/39-45 469688 Xn: 20/21/22-36/37/38 ...... 26-37/39 448362 ...... 22-24/25 469734 Xn: 20/21/22-36/37/38 ...... 26-37/39 448397 Xi: 36/37/38 ...... 26-36 469742 Xn: 20/21/22 ...... 36 448427 Xi: 36/37/38 ...... 26-36 470600 Xi: 36/37/38 ...... 26-37/39 448443 Xi: 36/37/38 ...... 26-36 471429 ...... 22-24/25 448532 Xi: 36/37/38 ...... 26-36 471631 Xi: 36/37/38 ...... 26-36 448540 Xi: 36/37/38 ...... 26-36 471860 Xi: 36/37/38 ...... 26-36 452823 Xi: 36/37/38 ...... 26-36/37 471879 Xi: 36/37/38 ...... 26-36 453382 Xn: 20/21/22 ...... 26-27-28-36/39 471895 Xi: 36/37/38 ...... 26-36 453692 Xi: 36/37/38 ...... 26-36 471909 Xn: 22-36/37/38-50/53 ...... 26-60-61 453714 C: 34 ...... 26-36/37/39-45 472522 C: 34 ...... 26-36/37/39-45 454680 F,Xi: 11-19-36/37/38 ...... 16-26 472719 Xi: 36 ...... 26-36 454699 F,Xi: 11-19-36/37/38 ...... 16-26 472891 Xi: 36/37/38 ...... 26-36 454877 Xi: 36/37/38 ...... 26-36 472905 Xi: 36/37/38 ...... 26-36 45510 T: 23/24/25-62-63 ...... 36/37-45 472972 Xi: 41-52/53 ...... 26-39-61 455172 T: 25-36/37/38 ...... 26-45 473367 Xi: 36/37/38 ...... 26-36 456136 Xi: 10-41 ...... 16-26-36 473391 Xi: 36/37/38 ...... 26-36 456144 Xi: 10-41 ...... 16-26-36 473405 Xi: 36/37/38 ...... 26-36 456152 Xi: 36/37/38 ...... 26-36 473758 C: 34 ...... 26-27-36/37/39-45 458538 Xi: 36/37/38 ...... 26-36 473960 C: 34 ...... 26-36/37/39-45 458546 Xi: 36/37/38 ...... 26-36 474533 Xi: 41 ...... 26-39 458554 Xn: 20/21/22 ...... 26-36 474789 T: 45-60-21/22-23-36/37/38-68 ...... 53-26-36/37/39-45 458562 Xn: 20/21/22 ...... 36 475548 Xi: 36/37/38 ...... 26-36 458570 Xn: 20/21/22 ...... 36 476986 Xi: 36/37/38 ...... 26-36 460028 Xi: 36/37/38 ...... 26-36 477087 F,Xn: 11-22-36/37/38 ...... 16-26 460508 Xi: 36/37/38 ...... 26-36 477109 Xi: 10-36/37/38 ...... 26-36/37/39 460516 Xi: 41 ...... 26-36 477141 Xi: 36/37/38 ...... 26-36 460524 Xi: 41 ...... 26-36 477168 Xi: 36/37/38 ...... 26-36 460826 ...... 23-24/25 477176 Xi: 36/37/38 ...... 26-36 461385 C: 34 ...... 26-36/37/39-45 477184 Xi: 36/37/38 ...... 26-36 461393 C: 34 ...... 26-36/37/39-45 477281 Xi: 37/38-41 ...... 26-36 461407 ...... 23-24/25 477346 Xi: 36/37/38 ...... 26-36 461415 ...... 23-24/25 479160 Xi: 36/37/38 ...... 26 461423 Xi: 36/37/38 ...... 26-36 479179 ...... 22-24/25 461431 Xi: 36/37/38 ...... 26-36 479284 C: 34 ...... 26-36/37/39-45 461458 Xi: 36/37/38 ...... 26-36 479292 C: 22-34 ...... 26-36/37/39-45 461466 Xi: 36/37/38 ...... 26-36 479772 Xi: 36/37/38 ...... 26-36 461474 Xi: 36/37/38 ...... 26-36 479926 Xi: 36/37/38 ...... 26-36 461482 Xi: 36/37/38 ...... 26-36 480819 T: 45-60-21/22-23-37/38-41-68 ...... 53-26-36/37/39-45 461490 Xi: 36/37/38 ...... 26-36 482641 T: 25 ...... 36/37/39-45 461504 Xi: 36/37/38 ...... 26-36 482757 Xi: 36/37/38 ...... 26-36 461520 Xi: 36/37/38 ...... 26 482846 Xi: 36/37/38 ...... 26-36 461555 Xi: 36/37/38 ...... 26-36 482854 Xi: 36/37/38 ...... 26-36 461563 Xi: 36/37/38 ...... 26-36 482900 Xi: 36/37/38 ...... 26-36 461601 Xi: 36/37/38 ...... 26-36 483796 Xi: 36/37/38 ...... 26-36/37 461628 Xi: 36/37/38 ...... 26-36 484334 Xi: 36/37/38 ...... 26-36 461636 Xi: 36/37/38 ...... 26-36 484342 Xi: 36/37/38 ...... 26-36 461644 Xi: 36/37/38 ...... 26-36 487244 Xi: 36/37/38 ...... 26-36 461652 Xi: 36/37/38 ...... 26-36 493740 Xn: 22-52/53 ...... 61 461660 Xi: 36/37/38 ...... 26-36 494186 Xi: 36/37/38 ...... 26-36 461679 Xi: 36/37/38 ...... 26-36 494577 C: 22-34 ...... 26-36/37/39-45 461687 Xi: 36/37/38 ...... 26-36 49554 Xn: 22-52/53 ...... 61 462039 C: 10-34 ...... 16-26-27-36/37/39-45 496057 Xi: 36/37/38 ...... 26-36 462101 C: 20/21/22-34 ...... 26-27-28-36/37/39-45 49671 F,Xn: 11-22-36/37/38 ...... 16-26 462403 Xi: 36/37/38 ...... 26-36 499587 Xi: 36/37/38 ...... 26-36 462624 Xi: 10-36/37/38 ...... 26-36 50047 Xi: 36/37/38 ...... 26-36 462632 Xi: 10-36/37/38 ...... 26-36 50048 Xi: 5-36/37/38 ...... 26-36 463396 Xi: 36/37/38 ...... 26-36 50282 C: 22-34 ...... 26-36/37/39-45 464007 F,T+: 11-26/27/28-36/38 ...... 16-26-36/37/39-45 510343 Xi: 36/37/38 ...... 26-36 464376 Xi: 36/37/38 ...... 26-36 510505 Xn: 22-37/38-41 ...... 26-39

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51241 Xn: 20/21/22-36/37/38 ...... 26-36/37 549479 Xi: 36/37/38 ...... 26-36 51401 Xn: 22-36/37/38 ...... 26 549487 Xi: 36/37/38 ...... 26-36 51432 C: 22-34 ...... 26-36/37/39-45 549495 Xi: 36/37/38 ...... 26-36 516015 Xi: 36/37/38 ...... 26-36 549525 Xi: 36/37/38 ...... 26-36 516058 Xi: 36/37/38 ...... 26-36 549533 Xi: 36/37/38 ...... 26-36 516120 Xi: 36/37/38 ...... 26-36 551015 Xi: 36/37/38 ...... 26-36 516376 Xi: 36/37/38 ...... 26-36 551074 Xi: 36/37/38 ...... 26-36 51989 Xi: 36-43 ...... 26-36/37 551082 Xi: 36/37/38 ...... 26-36 520497 Xi: 36/37/38 ...... 26-36 551090 Xi: 36/37/38 ...... 26-36 52057 Xi: 36/37/38 ...... 26 551147 Xi: 36/37/38 ...... 26-36 522880 Xi: 36/37/38 ...... 26-36 551155 Xi: 36/37/38 ...... 26-36

Risk & Safety 522902 F,Xi: 11-36/37/38 ...... 16-26-36 551953 Xi: 36/37/38 ...... 26-36 523720 Xi: 36/37/38 ...... 26-36 551961 Xi: 36/37/38 ...... 26-36 52560 ...... 23-24/25 551988 Xi: 36/37/38 ...... 26-36 527890 C: 22-34 ...... 26-36/37/39-45 551996 Xi: 36/37/38 ...... 26-36 52792 Xn: 22-36/37/38 ...... 26-36 552526 Xi: 36/37/38 ...... 26-37/39 52927 Xi: 36/37/38 ...... 26 552550 Xi: 36/37/38 ...... 26-36 531324 Xn: 20/21/22-36/37/38 ...... 23-26-27-28 552569 Xi: 36/37/38 ...... 26-36 531529 Xn: 22-36/37/38-40 ...... 26-36 554464 Xi: 36/37/38 ...... 26-36 532150 Xi: 36/37/38 ...... 26-36 554472 Xi: 36/37/38 ...... 26-36 532169 Xi: 36/37/38-50-53 ...... 26-36 554510 Xi: 36/37/38 ...... 26-36 532355 F,T: 20/21/22-34-40 ...... 16-26-27-36/37/39-45 55452 Xi: 36/37/38 ...... 26-36 532363 F,T: 20/21/22-34-40 ...... 16-26-27-36/37/39-45 554529 Xi: 36/37/38 ...... 26-36 532509 C: 34 ...... 26-27-36-45 554553 Xi: 36/37/38 ...... 26-36 532517 Xi: 36/37/38 ...... 26-36 554561 Xi: 36/37/38 ...... 26-36 532525 Xi: 36/37/38 ...... 26-36 554618 Xi: 36/37/38 ...... 26-36 532657 Xi: 36/37/38 ...... 26-36 554626 Xi: 36/37/38 ...... 26-36 532665 Xi: 36/37/38 ...... 26-36 554634 Xi: 36/37/38 ...... 26-36 532673 Xn: 20/21/22 ...... 26-36 554642 Xi: 36/37/38 ...... 26-36 532908 Xi: 36/37/38 ...... 26-36 55673 ...... 22-24/25 533106 Xi: 36/37/38 ...... 26-36 557900 Xn: 20/21/22-36/37/38 ...... 26-35-36 534552 Xi: 36/37/38 ...... 26-36 557951 ...... 24/25 534560 Xi: 36/37/38 ...... 26-36 557978 ...... 24/25 534579 Xi: 36/37/38 ...... 26-36 558028 10 ...... 534587 Xi: 36/37/38 ...... 26-36 558036 10 ...... 536229 C: 34 ...... 26-27-36/37/39 558044 10 ...... 536598 Xi: 36/37/38 ...... 26-36 558052 Xi: 10-37 ...... 24/25 536601 Xi: 36/37/38 ...... 26-36 558060 10 ...... 536628 Xi: 36/37/38 ...... 26-36 558079 Xi: 10-37 ...... 24/25 536644 Xi: 36/37/38 ...... 26-36 559032 C: 34 ...... 23-26-36/37/39-45 537306 Xi: 36/37/38 ...... 26-36 56193 Xi: 36/37/38 ...... 26-36 538167 Xi: 36/37/38 ...... 26-36 562653 Xi: 10-36/37/38 ...... 26-36/37/39 538183 Xi: 36/37/38 ...... 26-36 56308 Xi: 36/37/38 ...... 26 539007 Xi: 36/37/38 ...... 26-36 563382 Xi: 36/37/38-43 ...... 26-36/37 540005 Xi: 36/37/38 ...... 26-36 56437 Xi: 36/37/38 ...... 26 540013 Xi: 36/37/38 ...... 26-36 570516 Xi: 36/37/38 ...... 26-36 540021 F+,T: 45-20/21/22 ...... 53-45 570524 Xi: 36/37/38 ...... 26-36 540048 F+,T: 12-25 ...... 45 570532 Xi: 36/37/38 ...... 26-36 540056 T: 25-41 ...... 26-28-39-45 570540 Xi: 36/37/38 ...... 26-36 540064 T: 21-25-41 ...... 26-28-39-45 570559 Xi: 36/37/38 ...... 26-36 540072 T: 45-10-23/24/25-34-43 ...... 53-45 570842 Xn: 22 ...... 36/37 540080 T: 45-10-23/24/25-34-43 ...... 53-45 570877 Xi: 36/37/38 ...... 26-36 540099 T: 45-21-36 ...... 53-45 571326 Xi: 36/37/38 ...... 26-36 540102 T: 45-20/21-36/38 ...... 53-26-36/37-45 573213 Xn: 22 ...... 36 540110 T,N: 45-41-43-51/53-68 ...... 53-26-36/37/39-45-61 573337 Xi: 36/37/38 ...... 26-36 540129 T,N: 45-41-43-51/53-68 ...... 53-45-61 586250 Xi: 36/37/38 ...... 26-36 540781 Xi: 36/37/38 ...... 26-36 58923 10 ...... 540803 Xi: 36/37/38 ...... 26-36 591017 Xn: 22-37/38-41-42/43 ...... 26-36 542776 Xi,N: 43-50 ...... 24-35-37-61 591246 Xn: 36/37/38-42/43 ...... 26-36 543039 Xi: 36/37/38 ...... 26-36 591343 Xi: 36/37/38 ...... 26-36 545481 Xi: 36/37/38 ...... 26-36 591564 Xn: 22-37/38-41-42/43 ...... 26-36 545740 T: 25 ...... 26-36/37/39-45 591653 Xn: 36-42/43 ...... 26-36 545864 Xi: 36/37/38 ...... 26-36 591734 T: 25-36/37/38-42/43 ...... 26-36/37/39-45 545872 Xi: 36/37/38 ...... 26-36 591785 T: 25-41-42/43 ...... 22-26-36/37/39-45 546704 Xn: 22 ...... 591882 Xn: 22-37/38-41-42/43 ...... 26-36 546720 Xi: 10-36/37/38 ...... 26-36 592005 Xn: 22-37/38-41-42/43 ...... 26-36 548979 Xi: 36/37/38 ...... 26-36 62139 C: 34 ...... 26-36/37/39-45 54920 Xi: 36/37/38 ...... 26-36 63207 Xi: 37/38-41 ...... 26-39 54925 Xi: 36/37/38 ...... 26-36 634786 T: 25-37/38-41 ...... 26-39-45 549460 Xi: 36/37/38 ...... 26-36 634794 Xn: 22-41 ...... 26

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637505 Xn: 22-36/37/38 ...... 26 67176 Xi: 36/37/38 ...... 26 637513 Xn: 22-36/37/38 ...... 26 672033 Xn: 22 ...... 642002 Xn: 22 ...... 672297 Xi: 36/37/38 ...... 26 642118 Xn: 22 ...... 672408 Xi: 36/37/38 ...... 26

644064 Xn: 22-41-44 ...... 26-36/37/39 674761 Xi: 37/38-41 ...... 26-39 Safety & Risk 647233 Xn: 22-36/37/38-43 ...... 26-36/37/39 67519 Xn: 22-37/38-41 ...... 26-39 647241 Xi: 36/37/38 ...... 26-36 675377 Xn: 22 ...... 647446 Xi: 36/37/38 ...... 26-36 676322 Xi: 36 ...... 26 647462 Xn,N: 22-37/38-41-50/53 ...... 26-36/37/39-60-61 676691 Xi: 36 ...... 26 647470 Xn,N: 22-37/38-41-50/53 ...... 26-36/37/39-60-61 676705 Xi: 36 ...... 26 647497 Xi: 36/37/38 ...... 26-36 677302 Xn: 22-36/37/38 ...... 649147 F,C: 11-22-34 ...... 26-36/37/39-45 677310 Xn: 22-36/37/38 ...... 649961 Xi: 36/37/38 ...... 26-36 679097 F,C: 11-22-34 ...... 26-36/37/39-45 649988 Xi: 36/37/38 ...... 26-36 679380 Xi: 36/37/38 ...... 26 650838 Xn: 22-36/37/38 ...... 26 679399 Xn: 22-36/37/38 ...... 26-36/37 650846 Xn: 22-36/37/38 ...... 26-36 679410 Xn: 22-36/37/38 ...... 26 650919 Xi: 36/37/38 ...... 26-36 67948 F,Xn: 11-20/21/22-36/37/38 ...... 16-26-36 651559 Xi: 36/37/38 ...... 26-36 680087 F,Xn,N: 11-22-36/37/38-50 ...... 16-26-61 654639 Xi: 36/37/38 ...... 26-36 681202 Xn: 22-36 ...... 26 654647 Xi: 36/37/38 ...... 26-36 681229 N: 50 ...... 61 654655 T: 25-36/37/38 ...... 26-45 681369 Xn: 22 ...... 654663 T: 25-36/37/38 ...... 26-36-45 681709 Xn: 22-37/38-41 ...... 26-39 655236 Xn: 10-22-36/37/38 ...... 16-26-36 68249 Xi: 36/37/38 ...... 26-36 656356 Xi: 36/37/38 ...... 26-36 684325 Xn: 22 ...... 656364 Xi: 36/37/38 ...... 26-36 685291 T: 25 ...... 45 656704 Xn: 10-22-37/38-41 ...... 26-39 685828 Xn: 22-38-41 ...... 26-39 656712 Xn: 10-22-37/38-41 ...... 26-36/39 685836 Xn: 22-38-41 ...... 26-39 656747 Xn: 22-36/37/38 ...... 26-36 685844 Xn: 22-36/37/38 ...... 26 656755 Xn,N: 22-36/37/38-50 ...... 26-60-61 685852 Xn: 22-36/37/38 ...... 26 660051 Xn: 22-36/37/38 ...... 26-36 686271 Xn: 20/21/22-36/37/38 ...... 26 660078 Xn: 22-36/37/38 ...... 26-36 686298 Xn: 22-41-52/53 ...... 26-39-61 660108 C: 22-34 ...... 26-36/37/39-45 686301 Xn: 20/21/22-36/37/38 ...... 26 660116 C: 22-34 ...... 26-36/37/39-45 686336 Xn: 20/21/22-36/37/38 ...... 26 660205 T: 25 ...... 45 687278 T: 25-37/38-41 ...... 26-36/37/39-45 663336 Xi: 36/37/38 ...... 26-36 687324 Xi: 36/37/38 ...... 26 663344 Xi: 36/37/38 ...... 26-36 687332 Xi: 36/37/38 ...... 26-36/37 664073 Xn: 22-36/37/38-43 ...... 26-36/37 687340 Xi: 36/37/38 ...... 26-36/37 665061 Xn: 22 ...... 687367 Xi: 36/37/38 ...... 26 665088 Xn: 22-36/37/38 ...... 26 687588 T,N: 25-37/38-41-50 ...... 26-39-45-61 665614 F,Xn: 11-22-36/37/38 ...... 26-36 688525 T,N: 25-50 ...... 45-61 665797 F+: 12 ...... 3 689017 C: 34 ...... 26-36/37/39-45 666130 Xi: 37/38-41-43 ...... 26-36/37/39 69167 Xn: 22 ...... 666297 Xn: 22-37/38-41 ...... 26-39 69308 Xn: 22-37/38-41 ...... 26-39 666718 Xi: 36/37/38 ...... 26 694584 Xi: 36/37/38 ...... 26-36 667005 F+: 12 ...... 3 696404 Xn: 22-36 ...... 26 668427 F,C: 11-22-34 ...... 16-26-36/37/39-45 697680 Xi: 36-43 ...... 26-36/37 668516 F,C: 11-22-34 ...... 16-26-36/37/39-45 69784 Xi: 36/38 ...... 26 668796 C,N: 34-51/53 ...... 26-36/37/39-45-61 69796 Xi: 10-37-41 ...... 24-26-39 668818 Xi,N: 36/37/38-51/53 ...... 26-61 69819 Xi: 36/37/38 ...... 26-36 669660 C: 22-34 ...... 26-36/37/39-45 698660 Xi: 36-43 ...... 26-36/37 669768 Xn: 22 ...... 702498 Xn: 20/21/22-41 ...... 26-36/37-39 669865 Xn: 22 ...... 70940 Xi: 36/37/38 ...... 26-36 669989 Xn: 22 ...... 70942 Xi: 36/37/38 ...... 26-36 670057 Xn: 22-36/37/38 ...... 26 73525 Xi: 36-43 ...... 26-36/37 670170 Xn: 22-36/37/38 ...... 26 75914 Xn: 22 ...... 670219 Xi: 36/37/38 ...... 26 76477 Xn: 10-21/22-36/37/38-40 ...... 26-36/37 670286 Xi: 36/37/38 ...... 26 77301 Xi: 36/37/38 ...... 26-36 670324 Xi: 36/37/38 ...... 26 77429 10 ...... 670650 C: 34 ...... 26-36/37/39-45 77913 10 ...... 670766 C: 34 ...... 26-36/37/39-45 77914 C: 22-34 ...... 26-36/37/39-45 670863 Xn,N: 22-50 ...... 61 78803 Xi: 36/37/38 ...... 26-36 670987 Xn,N: 22-50 ...... 61 78972 Xi: 36/37/38 ...... 26-36 671126 Xn: 22 ...... 78974 Xi: 36/37/38 ...... 26-36 671223 Xn: 22 ...... 82253 Xi: 36/37/38 ...... 26-36 671274 C: 22-34 ...... 26-36/37/39-45 82579 Xn: 22 ...... 671312 Xn,N: 22-50 ...... 61 83903 Xi: 36/37/38 ...... 26-36 671436 Xn,N: 22-50 ...... 61 857300 F,Xn: 11-22-36/37/38 ...... 16-26 671606 Xi: 41 ...... 26-39 87437 Xi: 36/37/38 ...... 26-36 671649 C: 21/22-34 ...... 26-36/37/39-45 88808 10 ...... 671711 Xi: 41 ...... 26-39 89095 Xi: 36 ...... 26

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89231 Xn: 22 ...... C409 Xn: 22 ...... 91292 Xi: 36/37/38 ...... 26 E34102 Xi: 10-37-41 ...... 24-26-39 91724 C: 34 ...... 26-36/37/39-45 G2410 Xi: 36/37/38 ...... 26-36 91936 F,C: 11-20/21/22-35 ...... 26-36/37/39-45 I13901 F,Xi: 11-38 ...... 93786 C,N: 22-34-50 ...... 26-36/37/39-45-61 M1125 Xi: 37/38-41 ...... 26-39 95889 C: 34 ...... 26-36/37/39-45 M2004 ...... 22-24/25 A154 Xi: 36/37/38 ...... 26-36 M2780 Xi: 37/38-41 ...... 26-39 A6801 Xi: 36/37/38 ...... 26-36 M3000 Xi: 36/37/38 ...... 26-36 A70704 Xn: 22-36/37/38 ...... 26 M38583 10 ...... 16-27-36/37/39 A70909 Xn: 42/43 ...... 22-36/37 M3933 F,T: 11-23/24/25-39/23/24/25 ...... 7-16-36/37-45 A76206 C: 34 ...... 26-36/37/39-45 M39709 10 ...... 16-29-33

Risk & Safety A83407 Xn: 10-20 ...... 24/25 N3386 Xi: 36/37/38 ...... 26 B60002 Xi: 36/37/38 ...... 26-37/39 O1631 ...... 22-24/25 C003 T: 23/24/25 ...... 22-36/37/39-45 T109 Xi: 36/37/38 ...... 26 C2107 C: 34 ...... 26-36/37/39-45 V104 Xn: 20/21/22 ...... 36 C301 F: 11 ...... 16-33

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