methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 129163-30-0
• Molecular Formula: C₂₅H₃₀O₇S
• Molecular Weight: 474.575
• Mol file: 129163-30-0.mol

Synonyms:methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside

There total 1 articles about methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside 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: 86.0%

tributyl(methylthio)stannane (17314-32-8) + 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose (80738-50-7) → methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside (129163-30-0)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)97383-0

Reference yield: 90.0%

methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside (129163-30-0) + tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid (120312-09-6) → tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside (129163-31-1)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; copper(ll) bromide; In nitromethane; at 20 ℃; for 2h;

DOI:10.1016/0008-6215(92)85040-7

Reference yield:

methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside (129163-30-0) → 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / silver trifluoromethanesulfonate, tetrabutylammonium bromide, CuBr₂, molecular sieves 4A / nitromethane / 2 h / 20 °C

2: tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; silver trifluoromethanesulfonate; acetic acid; copper(ll) bromide; In tetrahydrofuran; nitromethane;

DOI:10.1016/0008-6215(92)85040-7

upstream raw materials:

tributyl(methylthio)stannane

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose

Downstream raw materials:

tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-D-glucopyranosyl fluoride