Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS No.: 417717-45-4
• Molecular Formula: C₂₃H₃₅BrO₇Si
• Molecular Weight: 531.516
• Mol file: 417717-45-4.mol

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside (386235-64-9) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester (417717-45-4)

Guidance literature:

With bromine; In dichloromethane; at -23 - 20 ℃;

DOI:10.1021/ol016713j

Reference yield:

phenyl 2,3-di-O-acetyl-4-O-benzyl-β-D-selenoglucopyranoside (386235-72-9) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester (417717-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 50 °C

2: Br₂ / CH₂Cl₂ / 0.5 h / -23 - 20 °C

With dmap; bromine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200500126

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester (417717-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 50 °C

2: 100 percent / bromine / CH₂Cl₂ / -23 - 20 °C

With dmap; bromine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016713j

upstream raw materials:

phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside

tert-butyldimethylsilyl chloride

phenyl 2,3-di-O-acetyl-4-O-benzyl-β-D-selenoglucopyranoside

phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-5-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-2-phenylselanyl-tetrahydro-pyran-4-yl ester

phenyl 2-O-acetyl-6-O-(4'-O-benzyl-2',3'-di-O-acetyl-6'-O-tri-isopropylsilyl-β-D-glucopyranosyl)-3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-selenoglucopyranoside