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

Base Information

• Chemical Name: 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
• CAS No.: 502185-64-0
• Molecular Formula: C₃₆H₅₁NO₁₂
• Molecular Weight: 689.8
• Mol file: 502185-64-0.mol

Synonyms: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

Chemical Property of 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

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)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 8 articles about 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 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: 80.0%

4-O-(2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-threo-hex-3-enopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (432038-81-8) → 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)

Guidance literature:

4-O-(2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-threo-hex-3-enopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal; With dimethylsulfide borane complex; for 2h;

With sodium hydroxide; dihydrogen peroxide; for 2h;

DOI:10.1016/S0040-4039(02)02232-3

Reference yield:

benzyl bromide (100-39-0) → 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)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 1.5 h

2.1: 79 percent / acetic acid / H₂O / 1.45 h / 40 °C

3.1: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 95 percent / dibutyltin oxide; tetrabutylammonium bromide / toluene / 5.5 h / Heating

5.1: 79 percent / sodium hydride; sulfuryldiimidazole / dimethylformamide / 4 h / -30 - 20 °C

6.1: boran - dimethyl sulfide complex / diethyl ether / 5 h / 20 °C

6.2: 64 percent / sodium hydroxide; hydrogen peroxide / H₂O / 2 h

With 1,1-sulfonyldiimidazole; potassium hydroxide; 18-crown-6 ether; dimethylsulfide borane complex; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1081/CAR-200030011

Reference yield:

4-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (263845-22-3) → 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)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 1.5 h

2.1: 79 percent / acetic acid / H₂O / 1.45 h / 40 °C

3.1: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 95 percent / dibutyltin oxide; tetrabutylammonium bromide / toluene / 5.5 h / Heating

5.1: 79 percent / sodium hydride; sulfuryldiimidazole / dimethylformamide / 4 h / -30 - 20 °C

6.1: boran - dimethyl sulfide complex / diethyl ether / 5 h / 20 °C

6.2: 64 percent / sodium hydroxide; hydrogen peroxide / H₂O / 2 h

With 1,1-sulfonyldiimidazole; potassium hydroxide; 18-crown-6 ether; dimethylsulfide borane complex; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1081/CAR-200030011

upstream raw materials:

4-O-(2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-threo-hex-3-enopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

benzyl bromide

4-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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

Downstream 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-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

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