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

Base Information

Chemical Name:4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
CAS No.:1590392-17-8
Molecular Formula:C₄₁H₅₃N₃O₁₁
Molecular Weight:763.885
Hs Code.:

Synonyms:4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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Chemical Property of 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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Technology Process of 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 10 articles about 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-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: 92.0%

: 1590392-16-7
4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

: 1590392-17-8
4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 0.75h; Inert atmosphere;
DOI:10.1016/j.carres.2014.01.020

Reference yield:

: 1590392-11-2
4-O-(3,6-di-O-benzyl-4-deoxy-2-O-p-methoxybenzyl-β-D-erhytrohex-4-enopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

: 1590392-17-8
4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 5 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

2.2: 12 h / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

4.2: 1 h / -30 °C / Inert atmosphere

5.1: sodium azide / N,N-dimethyl-formamide / 0.75 h / 100 °C / Inert atmosphere

With sodium azide; dimethylsulfide borane complex; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2014.01.020

Reference yield:

: 1590392-14-5
4-O-(3,4,6-tri-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

: 1590392-17-8
4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 1 h / -30 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 0.75 h / 100 °C / Inert atmosphere

With sodium azide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2014.01.020