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

Base Information

Chemical Name:4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal
CAS No.:1590392-15-6
Molecular Formula:C₄₁H₅₄O₁₂
Molecular Weight:738.873
Hs Code.:

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

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Chemical Property of 4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

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Technology Process of 4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

There total 8 articles about 4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-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: 76.0%

: 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

: 1590392-15-6
4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 1h;
DOI:10.1016/j.carres.2014.01.020

Reference yield:

: 1590392-13-4
4-O-(3,6-di-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

: 1590392-15-6
4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 12 h / 0 - 20 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

With 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

Reference yield:

: 1590392-10-1
4-O-(6-O-benzyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

: 1590392-15-6
4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; hexane / 0.33 h / 0 - 20 °C

2.2: 12 h / 0 - 20 °C

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

3.2: 2 h / 0 - 20 °C / Inert atmosphere

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

4.2: 12 h / 0 - 20 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

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