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

Base Information

• Chemical Name: phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside
• CAS No.: 386235-64-9
• Molecular Formula: C₂₉H₄₀O₇SeSi
• Molecular Weight: 607.678
• Mol file: 386235-64-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside 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: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + phenyl 2,3-di-O-acetyl-4-O-benzyl-β-D-selenoglucopyranoside (386235-72-9) → phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside (386235-64-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 50 ℃; for 12h;

DOI:10.1021/ol016713j DOI:10.1002/chem.200500126

Reference yield:

phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside (106023-50-1) → phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside (386235-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃SiH; PhBCl₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

2: 98 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 50 °C

With triethylsilane; dmap; 4 A molecular sieve; phenylborondichloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016713j

Reference yield:

phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-selenoglucopyranoside → phenyl 2,3-di-O-acetyl-4-O-benzyl-6-O-t-butyldimethylsilyl-β-D-selenoglucopyranoside (386235-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃SiH; PhBCl₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

2: 98 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 50 °C

With triethylsilane; dmap; 4 A molecular sieve; phenylborondichloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200500126

upstream raw materials:

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-2-bromo-6-(tert-butyl-dimethyl-silanyloxymethyl)-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

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