3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

Chemical Name:3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose
CAS No.:1380315-39-8
Molecular Formula:C₃₂H₃₇BrO₇
Molecular Weight:613.546
Hs Code.:

Synonyms:3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

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Chemical Property of 3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

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Technology Process of 3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

There total 5 articles about 3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose 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: 90.0%

: 91-13-4
α,α'-dibromo-o-xylene

: 3-O-benzyl-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

: 1380315-39-8
3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: 3-O-benzyl-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose; With 18-crown-6 ether; sodium hydride; In dichloromethane; mineral oil; at -10 ℃; for 0.166667h;

α,α'-dibromo-o-xylene; In dichloromethane; mineral oil; at -10 - 20 ℃; for 14h;
DOI:10.1002/ejoc.201101815

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 1380315-39-8
3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / toluene / 5 h / 90 °C

1.2: 90 °C

2.1: 18-crown-6 ether; sodium hydride / dichloromethane; mineral oil / 0.17 h / -10 °C

2.2: 14 h / -10 - 20 °C

With 18-crown-6 ether; sodium hydride; di(n-butyl)tin oxide; In dichloromethane; toluene; mineral oil;
DOI:10.1002/ejoc.201101815

Reference yield:

: 100-39-0
benzyl bromide

: 1380315-39-8
3-O-benzyl-5-O-(2-bromomethylbenzyl)-6-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 8 h / 20 °C

2.1: acetic acid / water / 2 h / 80 °C

3.1: di(n-butyl)tin oxide / toluene / 5 h / 90 °C

3.2: 90 °C

4.1: 18-crown-6 ether; sodium hydride / dichloromethane; mineral oil / 0.17 h / -10 °C

4.2: 14 h / -10 - 20 °C

With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1002/ejoc.201101815