p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Base Information

• Chemical Name: p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside
• CAS No.: 1269466-82-1
• Molecular Formula: C₃₃H₄₀O₆SSi
• Molecular Weight: 592.829

Synonyms:p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Chemical Property of p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Chemical Property:

Purity/Quality:

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Technology Process of p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

There total 6 articles about p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-55-6) → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside (1269466-82-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol200192d

Reference yield: 78.0%

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside + benzoic acid anhydride (93-97-0) → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside (1269466-82-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jacs.9b06830

Reference yield:

p-methylphenyl 2-O-benzoyl-3,4-O-benzylidene-1-thio-β-D-galactopyranoside → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside (1269466-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid / acetonitrile / 8 h / 20 °C

2: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; camphor-10-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ol200192d

upstream raw materials:

tert-butyldimethylsilyl chloride

p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

p-methylphenyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

p-tolyl 2-O-benzoyl-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-galactopyranosidede

p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

p-methylphenyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-3-O-benzyl-1-thio-β-D-xylopyranoside

N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside

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