sign in sign up
<<
Home , Chloroformate, Protecting group, Reagent, Trimethylsilyl

Please inquire for pricing and availability of listed products to our local sales representatives. 1 Protecting Agents

Protecting groups are of vital importance in . In ● Acylation Reagents many cases, reaction conditions will effect multiple functionalities, Acyl protecting groups are usually used for the protection of which necessitate the blocking of several functional groups to hydroxy groups and amino groups. Acetyl (Ac), benzoyl (Bz), and afford the correct synthetic transformation. However, protecting pivaloyl (Piv) groups are commonly chosen. Pivaloyl groups is group attachment and removal requires their own conditions as often selected when non-sterically hindered hydroxyl groups well as individual chemical properties, and appropriate selection need to be selectively protected due to the Piv groups large size. of the correct protecting agents is vitally important for synthetic Generally, acyl protecting groups are stable under acidic and strategy. The most useful protecting agents generally need oxidative conditions. Acyl protecting groups are usually several key properties: deprotected under basic or reductive conditions (DIBAL, LAH, - The protecting agents must selectively react with the desired etc.). requiring protection.

- The protecting groups must be introduced in high yields O O O without any side reactions. CH3 CH3 - The protected functional groups should be stable under CH3 CH3

various reaction conditions. Ac group Bz group Piv group - The protecting groups must be chemoselectively deprotected O under specific conditions without deprotection of other types X R2 O of protecting groups. R1 OH 1 2 Particularly in and for structurally complicated OH or DIBAL R O R compounds, designing the synthetic strategies frequently requires careful selection of protecting groups. Over time, a large array of protection groups have become available due in part to ● Acetalization Reagents, the highly specialized requirements needed in complex synthesis. Thioacetalization Reagents Many of these reagents and protection groups include specialized and thioacetals are most often used in the protection of conditions for attachment and removal that have high specificity carbonyl groups, particularly that of aldehydes and . The for a given functional and protection group. This brochure acetals and ketals are usually are introduced under acidic introduces a variety of protecting agents, which are sorted based conditions and take advantage of the equilibrium these exist on the methods used for their deprotection. under to install them. Acetals are stable under basic conditions and reductive conditions, and are additionally inert towards nucleophiles and organometallic reagents. Deprotection is ● Silylation Reagents usually carried out via hydrolysis under aqueous acidic conditions. Silyl groups are one of the most commonly used protecting Thioacetals have a wider synthetic resistance and are usually groups to block hydroxy functionalities, as well as for the stable under both acidic and basic aqueous conditions. The protection of carboxyl groups and amino groups. deprotection of thioacetals usually requires the addition of (TMS) and triethylsilyl (TES) are commonly used as general or mercury salts or hypervalent iodine compounds. short-term protecting groups, while triisopropylsilyl (TIPS), tert- butyldimethylsilyl (TBS or TBDMS) and tert-butyldiphenylsilyl R1O OR1 R1S SR1 (TBDPS) groups are used for introducing bulky substituents that R2 R2 R2 R2 are more robust. Silyl protecting groups are often readily acetals or ketals dithioacetals or dithioketals deprotected under acidic conditions, or by fluoride ions. O 2 2 2 R OH R R 2 CH3 C2H5 iPr CH3 Ph R OH O Si CH Si C H Si iPr Si tBu Si tBu 1 3 2 5 R + O H3O 1 CH3 C2H5 iPr CH3 Ph R

TMS group TES group TIPS group TBS (TBDMS) group TBDPS group

O SH SH 2 X SiR 3 S S R1 R1 OSiR2 R R OH 3 Hg or Ag salts R R F or I2 or (CF3CO2)2IPh

2 Please inquire for pricing and availability of listed products to our local sales representatives. Protecting Agents

● Alkoxymethylation Reagents ● 9-Fluorenylmethyloxycarbonylation Alkoxymethyl groups such as methoxymethyl (MOM) group are (Fmoc) Reagents generally used for the protection of hydroxy groups. They are 9-Fluorenylmethyloxycarbonyl (Fmoc) group is one of the most stable under basic and reducing conditions due to formally being commonly used protecting groups for amino groups in solid functionality. Alkoxymethyl groups are usually deprotected phase . It is readily deprotected by secondary by acid catalyzed hydrolysis. such as piperidine and is stable under acidic conditions. Of note, when a molecule contains both a Fmoc and Boc group, only the Boc group will be selectively removed under acidic conditions. OCH3 OEt OBn O

MOM group MEM group BOM group THP group O

Cl OCH3 O 1 1 R OH R O OCH3 H or Lewis acid Fmoc group

O

Fmoc-Cl 1 ● 1 R N O Tritylation (Tr) Reagents R NH2 H Trityl (Tr) groups are mainly used for the protection of hydroxy groups. They can selectively protect less sterically-hindered substrates due to their large size. They are relatively stable against bases, oxidizing agents, reducing agents and nucleophiles, and the deprotection is carried out under acidic ● Allyloxycarbonylation (Alloc) Reagents, hydrolysis conditions. Benzyloxycarbonylation (Cbz) Reagents, Benzylation (Bn) Reagents, and Allylation OCH3 (All) Reagents Allyloxycarbonyl (Alloc), benzyloxycarbonyl (Cbz), benzyl (Bn) and allyl (All) groups are commonly used for the protection of amino groups. These protecting groups are generally deprotected OCH3 by palladium catalysts.

O OCH3 O Tr group MMTr group DMTr group O O

Alloc group Cbz group Bn group Allyl group

Tr Cl Alloc-Cl O R1 OH R1 O RNH2 H or RN O Lewis acid cat. Pd or Ni H Hydrides

O Cbz-Cl

RNH2 RN O cat. Pd or Ni H H2 ● tert-Butoxycarbonylation (Boc) Reagents Bn-X tert-Butoxycarbonyl (Boc) group is one of the most commonly R O R OH used protective groups for amino groups in peptide synthesis. It cat. Pd, H2 is also used for the protection of hydroxy groups. It is stable under basic hydrolysis conditions and catalytic reduction conditions, allyl halide and is inert against various nucleophiles. It is commonly R OH R O base, then H+ deprotected under acidic conditions with trifluoroacetic acid. or cat. Pd, K2CO3 MeOH

O CH3 CH3

O CH3 Boc group

Boc2O O CH3 CH3 1 R NH2 1 R N O CH3 H H

Please inquire for pricing and availability of listed products to our local sales representatives. 3 Protecting Agents

●2,2,2-Trichloroethoxycarbonylation (Troc) ● Photolabile Protecting Reagents Reagents Photolabile protecting groups like D4970 can be introduced to The 2,2,2-trichloroethoxycarbonyl (Troc) group is used as a afford "caged" compounds and is most often employed in for hydroxy and amino groups. The Troc group is protecting bioactive molecules. The "caging" of bioactive generally deprotected by treatment with zinc powder or by molecule with photolabile protecting groups in particular have . proven to be a particularly useful tool in biochemical research. “Caged” compounds are inactivated with photolabile protecting O groups and can be activated by UV or visible light irradiation. Research towards controlling the topical expression of O CCl3 Troc group biomolecule activity using caged compounds has been recently reported and continues to be heavily investigated. To date, Troc-Cl O several classes of caged biomolecule have been synthesized 1 R NH2 1 R N O CCl3 and reported, including: , amino acids, biotin, and Zn, H+ H or sugars. electrolysis

NEt2

OH bioactive ● 2-(Trimethylsilyl)ethoxycarbonylation substance O h (Teoc) Reagents O O The 2-(trimethylsilyl)ethoxycarbonyl (Teoc) group is used as a Et2N O O protecting group for amines. Teoc groups can be deprotected [D4970] inactive active! with fluoride ion sources such as TBAF.

O CH3 CH3 Si O CH3 Teoc group

Teoc-Cl O CH3 CH3 References 1 Si R NH2 1 R N O CH3 F H Protective Groups in Organic Synthesis. 5th ed., ed. by T. W. Greene, P. G. M. Wuts, John Wiley & Sons, Inc., New York, 2014. A. Isidro-Llobet, M. Alvarez, F. Albericio, Chem. Rev. 2009, 109, 2455. M. Schelhaas, H. Waldmann, Angew. Chem. Int. Ed. 1996, 35, 2056. ● Sulfonylation Reagents K. Jarowicki, P. Kocienski, Contemp. Org. Synth. 1997, 4, 454. Sulfonyl groups have application as both protecting groups for hydroxy and amino groups, and for the of hydroxy functionalities.

O O

S CH3 S CH3 O O mesyl (Ms) group tosyl (Ts) group

O O NO2 S S CF3 O O nosyl (Ns) group trifulyl (Tf) group

Ms-Cl O R OH R O S CH3 Na(Hg), isopropanol O or CH3MgBr

4 Please inquire for pricing and availability of listed products to our local sales representatives. Protecting Agents

C0306 25mL 100mL 500mL B1087 5mL 25mL 250mL Trimethyl- silylation CH3 CH3 Silylation Reagents CH3 Si Cl CH3 Si Br (TMS) CH3 CH3 Reagents Chlorotrimethylsilane Bromotrimethylsilane CAS RN: 75-77-4 CAS RN: 2857-97-8 I0308 5g 25g T0871 5g 25g 250g T0585 25g 100g T0623 12mL T0801 5g 25g 100g

N N CH 3 O CH3 N N CH3

CH3 Si I CF3 S OSi CH3 CH3 Si CH3 CH3 Si CH3 CH3 Si N3 CH CH CH3 O CH3 3 3 CH3 Trimethylsilyl Iodide TMSOTf SIM Trimethylsilyl Azide CAS RN: 16029-98-4 CAS RN: 27607-77-8 CAS RN: 18156-74-6 SIM (in Anhydrous ） CAS RN: 4648-54-8 T0990 25mL 100mL 500mL B0511 10mL 100mL B0510 12mL B0830 5mL 25mL 100mL B3402 5mL 25mL 100mL CH CH 3 CH3 3 CH3

CH3 Si CH3 CH Si CH CH3 Si CH3 CH3 Si CH3 3 3 CH3 CH3 N N N N CH3 Si Cl CH3 CH3 CH3 CH3 CH3 Si CN CH3 CF3 O Si CH3 CH3 O Si CH3 CH3 O Si CH3 CF3 O Si CH3 CH CH 3 3 (99:1) CH3 CH3 CH3 Trimethylsilyl Cyanide BSA BSA (25% in ) BSTFA BSTFA-TMCS (99:1) CAS RN: 7677-24-9 CAS RN: 10416-59-8 CAS RN: 10416-59-8 CAS RN: 25561-30-2 CAS RN: 25561-30-2 H0089 25mL 100mL 500mL T0274 12mL B1245 5g 25g B1103 25g M0536 10g 25g

CH3 CH3

CH3 Si NH Si CH3

CH3 CH3 CH3 CH3 CH3 O CH3 O O CH3 CH3 CH CH Si NH Si CH 3 CH3 Si OSS O i CH3 (CH3)3Si Si(CH3)3 CH CN Si CH 3 3 N N 3 3 CH3 Si Cl CH O CH H H CH3 CH3 3 3 CH3 CH3 HMDS HMDS and TMCS Bis(trimethylsilyl) Sulfate BSU N-Methyl-N-TMS-acetamide CAS RN: 999-97-3 (in Anhydrous Pyridine) CAS RN: 18306-29-1 CAS RN: 18297-63-7 CAS RN: 7449-74-3 M0672 5mL 25mL T0492 25mL T1277 5mL 25mL T1535 5g T1752 5g 25g

CH3

CH3 Si CH3 CH3 N CH3 CH3 O CH3 N Si CH3 N CH CH N N 2 3 CH CH3 Si NCCF3 CH3 Si N 3 CH Si CH CH2CH3 O O O 3 3 CH3 CH 3 CH3 MSTFA TMS-DEA N-(Trimethylsilyl)morpholine 3-Trimethylsilyl-2-oxazolidinone 1-TMS-1H-benzotriazole CAS RN: 24589-78-4 CAS RN: 996-50-9 CAS RN: 13368-42-8 CAS RN: 43112-38-5 CAS RN: 43183-36-4 A0729 25mL 250mL V0067 25mL 100mL T0589 5g 25g 100g B5890 5g Triethyl- CH CH CH3 CH3 silylation CH2CH3 2 3 CH CH Si Br CH3 Si CH2CH CH2 CH2 CH Si CH3 (TES) CH3CH2 Si Cl 3 2 CH3 CH3 CH2CH3 CH2CH3 Allyltrimethylsilane Vinyltrimethylsilane Reagents Chlorotriethylsilane Bromotriethylsilane CAS RN: 762-72-1 CAS RN: 754-05-2 CAS RN: 994-30-9 CAS RN: 1112- 48-7 T1689 5g 25g T0662 25mL 250mL A2299 5g tert- B0995 5g 25g 100g Butyldimethyl- O CH2CH3 CH2CH3 CH2CH3 CH3 CH3 CF3 SOSi CH2CH3 CH3CH2 Si H CH3CH2 Si CH2CH CH2 silylation CH3 C Si Cl O CH2CH3 CH2CH3 CH2CH3 (TBS) CH3 CH3 Triethylsilyl Triflate Triethylsilane Allyltriethylsilane TBSCl CAS RN: 79271-56-0 CAS RN: 617-86-7 CAS RN: 17898-21-4 Reagents CAS RN: 18162-48-6 T1525 5g 25g B1043 1g 5g B1906 1g 5g B1150 1g 10g B2697 5g

CH3 CH3 N CH3 CH3 O Si C(CH3)3 CH3 Si CH3 CH CH O O CH CH 3 3 N CH3 N 3 3 CH3 CH3 CH3 CH3 Si C CH3 CH3 C Si OSCF3 CH3 O Si CH3 CF3 C N Si C CH3 C N

CH3 CH3 CH3 CH3 CH3 CH3 O CH3 CH3 CH3 N,O-Bis(tert-butyldimethylsilyl)- TBS Triflate 1-(tert-Butyldimethylsilyl)imidazole acetamide MTBSTFA TBS-BEZA CAS RN: 69739-34-0 CAS RN: 54925-64-3 CAS RN: 82112-21-8 CAS RN: 77377-52-7 CAS RN: 404392-70-7

Please inquire for pricing and availability of listed products to our local sales representatives. 5 Protecting Agents

T1078 5mL 25mL 250mL T1588 5g 25g T1533 5mL 25mL 100mL tert- Triisopropyl- Butyldiphenyl- silylation CH(CH3)2 O CH(CH3)2 CH(CH3)2 (CH3)2CH Si Cl CF3 SOSi CH(CH3)2 (CH3)2CH Si H silylation (TIPS) O CH(CH ) CH(CH3)2 3 2 CH(CH3)2 (TBDPS) Reagents TIPSCl Triisopropylsilyl Triflate Triisopropylsilane CAS RN: 13154-24-0 CAS RN: 80522-42-5 CAS RN: 6485-79-6 Reagents B1223 5mL 25mL 100mL B3566 5g B2898 1g 5g D0135 5g 25g

H C H3C H3C O 3 Other CH3 H C C Si H H COCSi S CF H3C CSiCl 3 3 3 H C O Silylation Cl Si CH2CH3 H3C 3 H3C Reagents CH3 TBDPSCl tert-Butyldiphenylsilane tert-Butyldiphenylsilyl Triflate Dimethylethylchlorosilane CAS RN: 58479-61-1 CAS RN: 33729-92-9 CAS RN: 92886-86-7 CAS RN: 6917-76-6 D1590 5mL 25mL D1594 5mL 25mL B2010 25mL D1827 25mL 100mL T2116 5g 25g

CH CH CH CH CH 3 CH CH3 3 3 3 3 3 CH3 CH3CH2CH2 Si Cl Si Cl CH3(CH2)3 Si Cl CH3(CH2)7 Si Cl CH C Si Cl CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Chlorodimethylpropylsilane Dimethylisopropylchlorosilane Butylchlorodimethylsilane Dimethyl-n-octylchlorosilane Chloro(dimethyl)thexylsilane CAS RN: 17477-29-1 CAS RN: 3634-56-8 CAS RN: 1000-50-6 CAS RN: 18162-84-0 CAS RN: 67373-56-2 C1468 25mL C1469 25mL D1560 25mL C1207 5mL 25mL B2334 5g

CH CH3 3 CH3 CH3 CH3

CH3(CH2)9 Si Cl CH3(CH2)11 Si Cl CH3(CH2)17 Si Cl NC CH2CH2CH2 Si Cl CH2 Si Cl CH CH3 CH3 CH3 CH3 3 (3-Cyanopropyl)- Chloro(decyl)dimethylsilane Chloro(dodecyl)dimethylsilane Dimethyloctadecylchlorosilane dimethylchlorosilane Benzylchlorodimethylsilane CAS RN: 38051-57-9 CAS RN: 66604-31-7 CAS RN: 18643-08-8 CAS RN: 18156-15-5 CAS RN: 1833-31-4 D1147 5mL 25mL D2262 1g 5g T3524 5g 25g D1390 25mL T0939 5g 25g

CH CH (CH ) CH CH3 2 3 2 3 3 CH3 Si Cl Si Cl CH Si Cl CH3(CH2)3 Si Cl Si Cl CH CH 3 3 CH2CH3 (CH2)3CH3 CH3 Chlorodimethylphenylsilane Chlorodiethylisopropylsilane Tributylchlorosilane Diphenylmethylchlorosilane Triphenylchlorosilane CAS RN: 768-33-2 CAS RN: 107149-56-4 CAS RN: 995-45-9 CAS RN: 144-79-6 CAS RN: 76-86-8 B1436 5mL 25mL C1492 5mL 25mL T0398 5g 25g 500g C2411 5g D0358 25mL 100mL 500mL

H3C CH(CH3)2 Cl Si(CH3)3 Cl H3C C O Si Cl HSiCl HCSi l (CH ) Si Si Cl CH3 Si CH3 H3C 3 3 CH(CH3)2 Cl Si(CH3)3 Cl tert-Butoxydiphenylchlorosilane Chlorodiisopropylsilane Trichlorosilane Chlorotris(trimethylsilyl)silane Dichlorodimethylsilane CAS RN: 17922-24-6 CAS RN: 2227-29-4 CAS RN: 10025-78-2 CAS RN: 5565-32-2 CAS RN: 75-78-5 D1976 5g 25g D2603 5g 25g D2469 5g D1995 5mL 10mL 25mL D0362 25g 100g 500g

Cl H C Cl CH Cl CH3 Cl CH3 3 3 Cl CH3CH2 Si CH2CH3 Si H3C CCSi C H3 CH3 Si (CH2)3Cl Si Cl Cl CH3 Cl CH3 H3C Cl CH3 Cl Dichlorodiethylsilane Dichlorodiisopropylsilane Di-tert-butyldichlorosilane 3-Chloropropyldichloromethylsilane Dichlorodiphenylsilane CAS RN: 1719-53-5 CAS RN: 7751-38-4 CAS RN: 18395-90-9 CAS RN: 7787-93-1 CAS RN: 80-10-4 D2334 5g 25g D1608 5g 25g B1688 5g 25g B1699 1mL 5mL D3135 1g 5g

CH3 CH3 (CH3)2HC CH(CH3)2 CH3 CH3 SiH(CH3)2 O C(CH ) O Cl Si OSi Cl Cl Si OSi Cl 3 3 Cl Si CH2CH2 Si Cl CF3 S OSi OSCF3 (CH3)2HC CH(CH3)2 CH3 CH3 SiH(CH3)2 CH3 CH3 O C(CH3)3 O 1,3-Dichloro-1,1,3,3- 1,3-Dichloro-1,1,3,3- tetramethyldisiloxane tetraisopropyldisiloxane 1,2-Bis(chlorodimethylsilyl)ethane 1,2-Bis(dimethylsilyl)benzene Di-tert-butylsilyl Ditriflate CAS RN: 2401-73-2 CAS RN: 69304-37-6 CAS RN: 13528-93-3 CAS RN: 17985-72-7 CAS RN: 85272-31-7

6 Please inquire for pricing and availability of listed products to our local sales representatives. Protecting Agents

A0082 100g 500g A0694 25g 100g 500g

N Acetylation O Acylation Reagents N Reagents CH3 Cl CCH3 O Acetyl Chloride N-Acetylimidazole CAS RN: 75-36-5 CAS RN: 2466-76-4 A1219 1g 5g A2301 5g M1168 5g P2192 1g 5g S0878 5g 25g N N O F F O N OO N C CH3 O O N CCH3 CH3 C O F CH3 C O N CH3 NCH3 O S S 1-Acetyl-1H-1,2,3- OCH3 F F O triazolo[4,5-b]pyridine 3-Acetylthiazolidine-2-thione N,N,N-Diacetylmethoxyamine Pentafluorophenyl Acetate N-Succinimidyl Acetate CAS RN: 107866-54-6 CAS RN: 76397-53-0 CAS RN: 128459-09-6 CAS RN: 19220-93-0 CAS RN: 14464-29-0 T0433 20mL 100mL 400mL T0670 5g 25g B0986 5g 25g M0671 1mL 5mL

N Trifluoro- O O OO OO acetylation N CF3 OCF3 C CF3 CF3 N CF3 CF3 NCF3 H O Reagents CH3 Trifluoroacetic Anhydride 1-(Trifluoroacetyl)imidazole Bistrifluoroacetamide MBTFA CAS RN: 407-25-0 CAS RN: 1546-79-8 CAS RN: 407-24-9 CAS RN: 685-27-8 P1894 5g 25g T0872 5mL T1531 5g T3174 1g 5g

F F O O O O N N N N Pivaloylation CF3 C O F CF3 C O SCF3 N N C CF3 CF3 SCH3 O C CF3 O Reagents F F Trifluoroacetyl O Pentafluorophenyl Trifluoroacetate Trifluorothioacetic Acid S-Ethyl Trifluoromethanesulfonate (Trifluoroacetyl)benzotriazole CAS RN: 14533-84-7 CAS RN: 383-64-2 CAS RN: 68602-57-3 CAS RN: 183266-61-7 P0677 25mL 500mL P1414 25mL 250mL B0078 25g 100g 500g B0105 25mL 500mL

O OO O O O C Cl CH3 CH3 Benzoylation (CH ) CCCl C OC 3 3 O CH3 CH3 Reagents CH3 CH3 Pivaloyl Chloride Pivalic Anhydride Benzoic Anhydride Benzoyl Chloride CAS RN: 3282-30-2 CAS RN: 1538-75-6 CAS RN: 93-97-0 CAS RN: 98-88-4 B3567 5g B3571 1g 5g P2229 1g 5g H0467 5g 25g

O O F F N O Other C O S CF3 O C N O N C O F Acylation C CF2CF2CF3 SS F F Reagents O Benzoyl Triflate 3-Benzoylthiazolidine-2-thione Pentafluorophenyl Benzoate 1-(Perfluorobutyryl)imidazole CAS RN: 36967-85-8 CAS RN: 70326-37-3 CAS RN: 1548-84-1 CAS RN: 32477-35-3 T0373 25g 100g 500g

O

Cl3CCCl

Trichloroacetyl Chloride CAS RN: 76-02-8 E0105 25g 500g P0485 500g Acetalization Reagents Acetalization OH CH3 Reagents HO OH Thioacetalization (Diol Derivatives) OH 1,2-Propanediol Reagents CAS RN: 107-21-1 CAS RN: 57-55-6

Please inquire for pricing and availability of listed products to our local sales representatives. 7 Protecting Agents

P0486 25g 100g 500g D0791 25g 500g B3563 5g 25g E0478 25g Acetalization CH3 CH3 CH3 Reagents HO OH HOCH2 CH2OH (CH3)3SiO OSi(CH3)3 CH3 Si O(CH2)2OSi CH3 CH3 CH3 (Carbonyl CH3 1,3-Propanediol 2,2-Dimethyl-1,3-propanediol 1,3-Bis(trimethylsilyloxy)propane 1,2-Bis(trimethylsilyloxy)ethane Derivatives) CAS RN: 504-63-2 CAS RN: 126-30-7 CAS RN: 17887-80-8 CAS RN: 7381-30-8 B2379 500g A0480 25mL 500mL D0626 25g 100g 500g A0057 25mL 500mL D1886 1mL 5mL O O O C H C H C H

OCH3 CH3O OCH3

CH3 CH3 CH3O OCH3 OCH3 OCH3 Benzaldehyde p-Anisaldehyde 2,4-Dimethoxybenzaldehyde 2,2-Dimethoxypropane 1,1-Dimethoxycyclopentane CAS RN: 100-52-7 CAS RN: 123-11-5 CAS RN: 613-45-6 CAS RN: 77-76-9 CAS RN: 931-94-2 D1372 25mL 100mL 500mL B1197 25mL 100mL 500mL A1247 25mL 500mL B3577 5g B1257 1mL 5mL OCH3 OCH3 CH CH OCH3 CH3O OCH3 OCH3 CH CH3CH3 3 OCH3 CH3 C Si O CH CH2 C OCH2 OCH3 CH3CH3

OCH3 tert-Butyl[4-(dimethoxymethyl)- 1,1-Dimethoxycyclohexane Benzaldehyde Dimethyl Acetal p-Anisaldehyde Dimethyl Acetal phenoxy]dimethylsilane 2-Benzyloxy-1-propene CAS RN: 933-40-4 CAS RN: 1125-88-8 CAS RN: 2186-92-7 CAS RN: 118736-04-2 CAS RN: 32783-20-3 I0303 25mL 100mL 500mL B1151 5g D2390 5g 25g D4208 1g 5g O O

CH3 CH3 CH2 Thio- S O O BF4 S S acetalization CH3 S S(CH2)3S S CH3 CH3 OCH3 S O O Reagents 1,3-Benzodithiolylium 3-(1,3-Dithian-2-ylidene)- 2-Methoxypropene Tetrafluoroborate 1,3-Di(p-tosylthio)propane 2,4-pentanedione CAS RN: 116 -11- 0 CAS RN: 57842-27-0 CAS RN: 3866-79-3 CAS RN: 55727-23-6 E0471 5g 25g E0479 5g P0763 25mL 100mL P1378 5g 25g

CH O O CH3 CH3 3 CH SSCH CH SS CH 3 2 2 3 CH3 Si S(CH2)2SSi CH3 HS SH SSi CH3 O O CH3 CH3 CH3 1,2-Di(p-tosylthio)ethane 1,2-Bis(trimethylsilylthio)ethane 1,3-Propanedithiol (Phenylthio)trimethylsilane CAS RN: 2225-23-2 CAS RN: 51048-29-4 CAS RN: 109-80-8 CAS RN: 4551-15-9 C0202 25g 100g 500g B2131 5g 25g B1207 25g 100g 500g

CH OCH Cl Alkoxymethylation 2 2 Br OCH Reagents Cl OCH3 3 Chloromethyl Methyl Bromomethyl Methyl Ether Benzyl Chloromethyl Ether CAS RN: 107-30-2 CAS RN: 13057-17-5 CAS RN: 3587-60-8 C0201 25g 100g 500g C2412 5g C1339 5mL 25mL E0193 25mL 100mL 500mL M0680 25mL 500mL

CH3 CH3O Cl OCH3 Cl O CCl3 CH3 Si CH2CH2OCH2Cl CH3 O CH2 OCl CH3 Chloromethyl Chloromethyl Ethyl Ether 2,2,2-Trichloroethyl Ether SEM-Chloride Ethyl Vinyl Ether MEM-Chloride CAS RN: 3188-13-4 CAS RN: 69573-75-7 CAS RN: 76513-69-4 CAS RN: 109-92-2 CAS RN: 3970-21-6 M0681 5g D0555 25mL 100mL 500mL

CH2CH3

CH3OCH2CH2OCH2 N CH2CH3 Cl CH2CH3 O (2-Methoxyethoxymethyl)- triethylammonium Chloride 3,4-Dihydro-2H-pyran CAS RN: 60043-43-8 CAS RN: 4551-15-9

8 Please inquire for pricing and availability of listed products to our local sales representatives. Protecting Agents

C0308 25g 100g 500g T0512 25g 100g T3432 1g 5g

Tritylation (Tr) CCl CBr P CCl Reagents Trityl Chloride Trityl Bromide Trityl Chloride Resin cross- CAS RN: 76-83-5 CAS RN: 596-43-0 linked with 1% DVB M0790 25g 250g D1612 5g 25g D2504 25g B1702 5g 25g T1071 5g 25g

O Br O C O C O C

CH3O CCl CH3O C Cl CCl

Cl Br O C O Tris[4-(phenylcarbonyloxy)- 4-Methoxytrityl Chloride DMT-Cl OCH3 2-Chlorotrityl Chloride 9-Bromo-9-phenylfluorene phenyl]methyl Bromide CAS RN: 14470-28-1 CAS RN: 40615-36-9 CAS RN: 42074-68-0 CAS RN: 55135-66-5 CAS RN: 86610-66-4 T1526 1g

O Cl N CBr Cl O 3 4,4',4''-Tris(4,5-dichloro- phthalimido)trityl Bromide CAS RN: 91898-93-0 D1547 25g 100g 500g D3878 100g 500g D3879 100mL 500mL tert- CH3 O O CH3 CH3 O O CH3 CH3 O O CH3 Butoxycarbonylation CH3 C O C O C OCCH3 CH3 C O C O C OCCH3 CH3 C O C O C OCCH3 (Boc) Reagents CH3 CH3 CH3 CH3 CH3 CH3 Boc2O Boc2O (ca. 30% in Dioxane) Boc2O (ca. 30% in ) CAS RN: 24424-99-5 CAS RN: 24424-99-5 CAS RN: 24424-99-5 D3880 100g 400g 500g B0916 10g B0988 5g 25g B1089 5g 25g B1969 5g 25g

CN O N CH3 N CNOCOC(CH3)3 CH3 O O CH3 N N N N CH3 CH3 C O C O C OCCH3 O C OC(CH3)3 C OCCH3 CH3 CH3 CH3 NSC OC(CH3)3 O O CH3

Boc2O (ca. 30% in Toluene) N-Boc-imidazole Boc-ON 2-Boc-thio-4,6-dimethylpyrimidine 1-Boc-1,2,4-triazole CAS RN: 24424-99-5 CAS RN: 49761-82-2 CAS RN: 58632-95-4 CAS RN: 41840-28-2 CAS RN: 41864-24-8 B3590 5g 25g C0933 25g 250g C1573 5g

O O CH O CH 3 O CH3 3 N OCO CCH3 O C O C CH3 H2NHN C OCCH3 CH3 CH3 CH O 3 N-(tert-Butoxycarbonyloxy)- tert-Butyl Phenyl Carbonate Boc-hydrazine phthalimide CAS RN: 6627-89-0 CAS RN: 870-46-2 CAS RN: 15263-20-4 F0197 5g 25g 100g F0239 5g 25g F0689 1g 5g

O 9-Fluorenylmethyloxy O carbonylation (Fmoc) CH2OCO N CH2OCCl O CH2OC NH2 O Reagents O Fmoc-Cl Fmoc-OSu Fmoc-NH2 CAS RN: 28920-43-6 CAS RN: 82911-69-1 CAS RN: 84418-43-9 F0871 5g F0872 5g 25g F0936 1g 5g

N N N F F O

O C OCH2 CH2O C O F

O CH2O C NHNH2 F F O Fmoc-OBt Fmoc-hydrazine Fmoc-OPfp CAS RN: 82911-71-5 CAS RN: 35661-51-9 CAS RN: 88744-04-1

Please inquire for pricing and availability of listed products to our local sales representatives. 9 Protecting Agents

A1268 25g 500g A2302 5g 25g Allyloxycarbonylation Reagents, Allyloxy- O O O Benzyloxycarbonylation Reagents, carbonylation CH2 Benzylation Reagents, (Alloc) Cl O CH2 CHCH2OC O N O Reagents Allyl Allyl N-Succinimidyl Carbonate Allylation Reagents CAS RN: 2937-50-0 CAS RN: 135544-68-2 A2303 5g 25g P1277 1g 5g B3021 25g 250g C0176 25mL 500mL O O

Benzyloxy- CH2OC Cl CH2OCCl O OO carbonylation CH CHCH OCO CH2 CH2 2 2 OOO (Cbz) Benzyl Chloroformate Allyl Phenyl Carbonate Diallyl Dicarbonate Reagents Benzyl Chloroformate (30-35% in Toluene) CAS RN: 16308-68-2 CAS RN: 115491-93-5 CAS RN: 501-53-1 CAS RN: 501-53-1 B3574 5g 25g C1124 25g 250g C1131 10g C1564 5g 25g C1591 1g 5g

Cl O O O O O O O CH2OCO N CH2OCO CH2OCON CH2OC NHNH2 O2NOC OCH2 O O N-(2-Chlorobenzyloxycarbonyloxy)- Benzyl Phenyl Carbonate Cbz-OSu succinimide Benzyl Carbazate Benzyl 4-Nitrophenyl Carbonate CAS RN: 28170-07-2 CAS RN: 13139-17-8 CAS RN: 65853-65-8 CAS RN: 5331-43-1 CAS RN: 13795-24-9 C1600 1g 5g P1281 5g 25g B0412 25g 500g B0411 25g 100g 500g

Benzylation CH2Cl CH2Br O OO CH OCOC OCH CH2OCOCH2 2 2 (Bn) Reagents Dibenzyl Carbonate Dibenzyl Dicarbonate Benzyl Bromide CAS RN: 3459-92-5 CAS RN: 31139-36-3 CAS RN: 100-44-7 CAS RN: 100-39-0 B1483 25g B3234 1g 5g B3361 1g 5g M0676 25mL 100mL M2016 5g 25g

CH2Cl

N OCH2 NH NH CF3 CH3 CH O C N Cl3C C OCH2 OCH3 Cl3C C OCH2 2 CF3SO3 2-Benzyloxy-1-methylpyridinium OCH Benzyl 2,2,2-Trifluoro- Triflate (This is only 3 4-Methoxybenzyl Benzyl 2,2,2-Trichloroacetimidate N-phenylacetimidate available in Japan.) 4-Methoxybenzyl Chloride 2,2,2-Trichloroacetimidate CAS RN: 81927-55-1 CAS RN: 952057-61-3 CAS RN: 882980-43-0 CAS RN: 824-94-2 CAS RN: 89238-99-3 N0181 25g 100g 500g C0274 25mL 500mL B0643 25g 500g A2186 5g

CH2Br Allylation NH CH2 CH2 (All) Cl Br Cl3CCOCH2CH CH2

NO2 Reagents 4-Nitrobenzyl Bromide Allyl Chloride Allyl Bromide Allyl 2,2,2-Trichloroacetimidate CAS RN: 100-11-8 CAS RN: 107-05-1 CAS RN: 106-95-6 CAS RN: 51479-73-3 C0795 25g 250g T2713 5g

O 2,2,2-Trichloroethoxy- O N O O C OCH CCl carbonylation (Troc) Cl O CCl3 2 3 O Reagents N-Succinimidyl 2,2,2-Trichloroethyl Chloroformate 2,2,2-Trichloroethyl Carbonate CAS RN: 17341-93-4 CAS RN: 66065-85-8 T2544 1g 5g T2590 1g 5g T2591 1g 5g

NO2 N 2-(Trimethylsilyl)- N O N N O N N ethoxycarbonylation (CH3)3SiCH2CH2OCON C OCH2CH2Si(CH3)3 O C OCH2CH2Si(CH3)3 (Teoc) Reagents O O O Teoc-NT Teoc-OBt Teoc-OSu CAS RN: 1001067-09-9 CAS RN: 113306-55-1 CAS RN: 78269-85-9

10 Please inquire for pricing and availability of listed products to our local sales representatives. Protecting Agents

T2872 5g

O CH3

O2N O C OCH2CH2 Si CH3

CH3

Teoc-ONp CAS RN: 80149-80-0 M0094 25g 500g Mesylation Tosylation Sulfonylation O (Ms) CH3 S Cl (Ts) Reagents Reagents O Reagents Mesyl Chloride CAS RN: 124-63-0 T0272 25g 500g T1485 5g 25g T1985 5g 25g T3187 1g 5g

SO Cl 2 N Triflation O O N N O CH S OS CH N S CH 3 3 SO2 CH3 3 (Tf) O O N O CH3 Reagents p-Toluenesulfonyl Chloride p-Toluenesulfonic Anhydride 1-(p-Toluenesulfonyl)imidazole 1-(p-Toluenesulfonyl)-1,2,4-triazole CAS RN: 98-59-9 CAS RN: 4124-41-8 CAS RN: 2232-08-8 CAS RN: 13578-51-3 T1027 5g 25g T1100 10g 25g 250g B1865 5g 25g B1871 5g N0993 5g 25g

OSO2CF3 Cl O O

CF SO Cl SO2CF3 SO2CF3 3 2 CF3 S OSCF3 N N NN

O O SO2CF3 SO2CF3 NO2 Trifluoromethanesulfonyl Chloride Trifluoromethanesulfonic Anhydride Comins Triflating Reagent 2-Pyridyltriflimide 4-Nitrophenyl Triflate CAS RN: 421-83-0 CAS RN: 358-23-6 CAS RN: 145100-51-2 CAS RN: 145100-50-1 CAS RN: 17763-80-3 P1257 5g 25g T2985 1g 5g T3167 1g 5g T3177 1g 5g

O O N N Nosylation CF3 S NSCF3 O N N N O O CF3 S NH SO CF SO CF (Ns) O 2 3 2 3 1-(Trifluoromethanesulfonyl)- 1-(Trifluoromethanesulfonyl)- Reagents Phenyl Triflimide Trifluoromethanesulfonanilide 1H-benzotriazole imidazole CAS RN: 37595-74-7 CAS RN: 456-64-4 CAS RN: 117632-84-5 CAS RN: 29540-81-6 N0142 25g 100g 500g N0144 5g 25g 100g B0036 25g 500g M0071 25g 100g 500g

SO Cl SO2Cl SO2Cl Other 2 SO2Cl NO2 CH3 CH3 Sulfonylation

NO2 Reagents CH3 2-Nitrobenzenesulfonyl Chloride 4-Nitrobenzenesulfonyl Chloride Benzenesulfonyl Chloride 2-Mesitylenesulfonyl Chloride CAS RN: 1694-92-4 CAS RN: 98-74-8 CAS RN: 98-09-9 CAS RN: 773-64-8 T0459 25g 500g C0924 5g 25g B0848 5g 25g B1128 1g 5g 25g B1931 5g 25g

SO2Cl CH3 CH3 CH CH SO2Cl SO2Cl CH3 CH3 O SO2Cl O O

CH3 Cl SCH2Cl S O S CH SO Cl CH3 O 2 O O 2,4,6-Triisopropylbenzenesulfonyl Chloride Chloromethylsulfonyl Chloride 1,3-Benzenedisulfonyl Chloride 1,2-Benzenedisulfonyl Dichloride Benzenesulfonic Anhydride CAS RN: 6553-96-4 CAS RN: 3518-65-8 CAS RN: 585-47-7 CAS RN: 6461-76-3 CAS RN: 512-35-6 P0934 5g 25g

SO2Cl F F

F F F Pentafluorobenzenesulfonyl Chloride CAS RN: 832-53-1

Please inquire for pricing and availability of listed products to our local sales representatives. 11 Protecting Agents

B5008 200mg B5738 250mg 1g D4970 200mg

CH2Br CH2OH CH2OH Photolabile Protection Br CH3CH2 CH3CH2 N O O HO O O N O O Reagents CH3CH2 CH3CH2 4-(Bromomethyl)- 6-Bromo-7-hydroxy- 7-(Diethylamino)- 7-(diethylamino)coumarin 4-(hydroxymethyl)coumarin 4-(hydroxymethyl)coumarin CAS RN: 1256259-14-9 CAS RN: 223420-41-5 CAS RN: 54711-38-5 D5477 1g 5g N1069 1g 5g N1132 1g 5g N1133 1g 5g O CH3 C CH3 CH3 OH CH3 OH NO2 O HO NO2 NO2 CH O O 3 O2N OCH3 4',5'-Dimethoxy- 2'-nitroacetophenone α-Methyl-6-nitropiperonyl 1-(2-Nitrophenyl)ethanol 2-(2-Nitrophenyl)propan-1-ol CAS RN: 4101-32-0 CAS RN: 159873-64-0 CAS RN: 3205-25-2 CAS RN: 64987-77-5 A1853 1g 5g B1496 5mL 25mL B4587 200mg 1g

O O O NH CH3 N N Other Protecting C CH3 Cl CCO CCH CH3 3 3 Cl N O Reagents CH3 O CH3 2-Acetyldimedone tert-Butyl 2,2,2-Trichloroacetimidate DBT-Cl CAS RN: 1755-15-3 CAS RN: 98946-18-0 CAS RN: 851030-18-7 C0041 25g 500g C0174 25mL 500mL C0597 25g 100g 500g C0608 25g 100g C1172 25mL 500mL

O Cl Cl CH OOCH O PCl 3 3 CH2 ClCH2SCH3 O CH3 2-Chloroethyl Vinyl Ether (stabilized with MEHQ + Diethyl Carbonate Triethanolamine) Chlorodiphenylphosphine Chloromethyl Methyl Sulfide 2-Chloroethyl Ethyl Ether CAS RN: 105-58-8 CAS RN: 110-75-8 CAS RN: 1079-66-9 CAS RN: 2373-51-5 CAS RN: 628-34-2 O0068 25mL 500mL

OCH3

HCOCH3

OCH3 Trimethyl Orthoformate CAS RN: 149-73-5

R5114E 20190207