4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal

Base Information

• Chemical Name: 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal
• CAS No.: 1245785-38-9
• Molecular Formula: C₃₃H₄₅NO₁₂
• Molecular Weight: 647.72
• Mol file: 1245785-38-9.mol

Synonyms:4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal

Chemical Property of 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal

There total 2 articles about 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal 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: 94.0%

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (1245785-36-7) → 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal (1245785-38-9)

Guidance literature:

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal; With di(n-butyl)tin oxide; In toluene; for 20h; Reflux;

With N-Bromosuccinimide; In chloroform; at 20 ℃;

DOI:10.1016/j.bmcl.2010.05.109

Reference yield:

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (502185-64-0) → 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal (1245785-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / water / 4 h / 40 °C

2.1: di(n-butyl)tin oxide / toluene / 12 h / Reflux; Dean-Stark

2.2: 0.5 h / 0 - 20 °C

With di(n-butyl)tin oxide; acetic acid; In water; toluene;

DOI:10.1002/ejoc.201402555

Reference yield:

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-D-xylo-hexos-5-ulose dimethyl acetal (1245785-38-9) → C28H35NO11

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃;

DOI:10.1016/j.bmcl.2010.05.109

upstream raw materials:

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Downstream raw materials:

4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-N-benzyl-2,3,6-tri-O-acetyl-1,5-di-deoxy-1,5-imino-D-glucitol