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. 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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. 2 70978 ChemFiles 9.3 cover.indd 2 6/18/2009 7:49:58 AM Heterocyclic Building Blocks Furans Heterocyclic Building Blocks (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. Rare Chemical Library items may also be packed to order through DiscoveryCPR. 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] Heterocyclic Building Blocks 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