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

Base Information

• Chemical Name: 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
• CAS No.: 1269466-99-0
• Molecular Formula: C₅₉H₆₆O₁₁SSi
• Molecular Weight: 1011.32
• Mol file: 1269466-99-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 65.0%

4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside (1269466-61-6) + p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside (1269466-90-1) → 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 (1269466-99-0)

Guidance literature:

4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside; p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside; With N-iodo-succinimide; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol200192d

Reference yield:

4-methylphenyl 1-thio-β-D-xylopyranoside (67803-94-5) → 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 (1269466-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -40 °C / Molecular sieve; Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: N-iodo-succinimide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

With triethylsilane; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1021/ol200192d

Reference yield:

p-methylphenyl 2,3,4-tri-O-trimethylsilyl-1-thio-β-D-xylopyranoside (1269466-45-6) → 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 (1269466-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -40 °C / Molecular sieve; Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: N-iodo-succinimide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

With triethylsilane; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/ol200192d

upstream raw materials:

4-methylphenyl 1-thio-β-D-xylopyranoside

p-methylphenyl 3-O-benzyl-1-thio-β-D-xylopyranoside

4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside

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

Downstream raw materials:

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

C₇₂H₈₃NO₁₄Si