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

Base Information

Chemical Name:3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose
CAS No.:1380315-52-5
Molecular Formula:C₃₂H₃₇BrO₇
Molecular Weight:613.546
Hs Code.:

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

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

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

There total 7 articles about 3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-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%

: 222844-98-6
3-O-benzyl-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

: 626-15-3
1,3-bis-(bromomethyl)benzene

: 1380315-52-5
3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: With 18-crown-6 ether; sodium hydride; In dichloromethane; mineral oil; at -10 - 20 ℃; for 14h; Inert atmosphere;
DOI:10.1002/ejoc.201101815

Reference yield:

: 1380315-47-8
3-O-benzyl-5-O-(4-methoxybenzyl)-6-O-triphenylmethyl-1,2-O-isopropylidene-α-D-glucofuranose

: 1380315-52-5
3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol; dichloromethane

2: 18-crown-6 ether; sodium hydride / dichloromethane; mineral oil / 14 h / -10 - 20 °C / Inert atmosphere

With 18-crown-6 ether; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; mineral oil;
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

: 1380315-52-5
3-O-benzyl-6-O-(3-bromomethylbenzyl)-5-O-(4-methoxybenzyl)-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C

2: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 10 h / 20 °C

3: toluene-4-sulfonic acid / methanol; dichloromethane

4: 18-crown-6 ether; sodium hydride / dichloromethane; mineral oil / 14 h / -10 - 20 °C / Inert atmosphere

With pyridine; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201101815