(4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 942044-42-0
• Molecular Formula: C₃₄H₃₄O₆S
• Molecular Weight: 570.706
• Mol file: 942044-42-0.mol

Synonyms:(4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

There total 10 articles about (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 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%

4-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-benzyl-1-thio-β-D-glucopyranoside (942043-30-3) → (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (942044-42-0)

Guidance literature:

4-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-benzyl-1-thio-β-D-glucopyranoside; With sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 2h; Molecular sieve; Inert atmosphere;

With hydrochloric acid diethyl ether; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol5036563

Reference yield: 70.0%

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside (942043-17-6) + acetic anhydride (108-24-7) + benzaldehyde (100-52-7) + β-naphthaldehyde (66-99-9) + benzoic acid anhydride (93-97-0) → p-tolyl 2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (942044-41-9) + (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (942044-42-0) + C33H34O6S (942044-44-2) + C38H36O6S (942044-45-3)

Guidance literature:

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside; benzaldehyde; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 2h; Molecular sieve;

benzaldehyde; β-naphthaldehyde; With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 5h; Combinatorial reaction / High throughput screening (HTS);

acetic anhydride; benzoic acid anhydride; With hydrogenchloride; sodium cyanoborohydride; trimethylsilyl trifluoromethanesulfonate; more than 3 stages;

Reference yield: 70.0%

p-methylphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside → (4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (942044-42-0)

Guidance literature:

p-methylphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside; With triethylsilane; trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 0.333333h;

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1039/c5ob02226f

upstream raw materials:

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside

acetic anhydride

benzaldehyde

β-naphthaldehyde