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

Base Information

Chemical Name: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
CAS No.:432038-81-8
Molecular Formula:C₃₆H₄₉NO₁₁
Molecular Weight:671.785
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 79.0%

: 791837-64-4
4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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

Guidance literature:: sodium hydride; N,N`-sulfuryldiimidazole; In N,N-dimethyl-formamide; at 0 ℃; for 24h;
DOI:10.1016/S0040-4039(02)00118-1

Reference yield:

: 100-39-0
benzyl bromide

: 432038-81-8
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

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 1.5 h

2: 79 percent / acetic acid / H₂O / 1.45 h / 40 °C

3: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

4: 95 percent / dibutyltin oxide; tetrabutylammonium bromide / toluene / 5.5 h / Heating

5: 79 percent / sodium hydride; sulfuryldiimidazole / dimethylformamide / 4 h / -30 - 20 °C

With 1,1-sulfonyldiimidazole; potassium hydroxide; 18-crown-6 ether; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1081/CAR-200030011

Reference yield:

: 263845-22-3
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

: 432038-81-8
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

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 1.5 h

2: 79 percent / acetic acid / H₂O / 1.45 h / 40 °C

3: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 20 °C

4: 95 percent / dibutyltin oxide; tetrabutylammonium bromide / toluene / 5.5 h / Heating

5: 79 percent / sodium hydride; sulfuryldiimidazole / dimethylformamide / 4 h / -30 - 20 °C

With 1,1-sulfonyldiimidazole; potassium hydroxide; 18-crown-6 ether; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1081/CAR-200030011