p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 1352561-53-5
• Molecular Formula: C₃₁H₃₄O₇S
• Molecular Weight: 550.673
• Mol file: 1352561-53-5.mol

Synonyms:p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

There total 1 articles about p-tolyl 4,6-di-O-acetyl-2,3-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: 93.0%

acetic anhydride (108-24-7) + 4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (596087-18-2) → p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (1352561-53-5)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2013.06.009

Reference yield: 89.0%

p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (1352561-53-5) + 4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside (1093430-43-3) → p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-3-O-benzoyl-β-D-glucopyranoside (1453195-45-3)

Guidance literature:

p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside; 4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside; In dichloromethane; at -40 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; sulfuric acid; silica gel; In dichloromethane; at -40 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2013.06.009

Reference yield:

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside (850416-39-6) + methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (1352561-53-5) → methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside (1352561-88-6) + methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside + methyl (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 - 0 ℃; for 3h; optical yield given as %de; Molecular sieve;

DOI:10.1021/jo201586r

upstream raw materials:

acetic anhydride

4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside

C₅₁H₅₆O₁₃

p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside

p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-3-O-benzoyl-β-D-glucopyranoside