4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

Base Information

Chemical Name:4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside
CAS No.:241471-13-6
Molecular Formula:C₄₀H₄₅BrO₆
Molecular Weight:701.698
Hs Code.:

Synonyms:4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

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Chemical Property of 4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

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Technology Process of 4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

There total 1 articles about 4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside 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: 78.0%

: ((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-yl)-methanol

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

: 241471-13-6
4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

Guidance literature:: With 15-crown-5; sodium hydride; In dichloromethane; at -17 ℃; for 8h;
DOI:10.1021/jo990132e

Reference yield: 15.0%

: 241471-13-6
4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

: 17791-36-5
methyl 2,3-di-O-benzyl-α-D-glucopyranoside

: 241471-14-7
4-penten-1-yl 6-O-[3-(methyl 2,3-di-O-benzyl-α-D-glucopyranoside-6-yloxymethyl)-benzyl]-2,3,4-tri-O-benzyl-α/β-D-glucopyranoside

: 241470-92-8
4-penten-1-yl 6-O-[3-(methyl 2,3-di-O-benzyl-α-D-glucopyranoside-4-yloxymethyl)-benzyl]-2,3,4-tri-O-benzyl-α/β-D-glucopyranoside

Guidance literature:: With 15-crown-5; sodium hydride; In dichloromethane; for 2h;
DOI:10.1021/jo990132e

Reference yield:

: 241471-13-6
4-penten-1-yl 2,3,4-tri-O-benzyl-6-O-(3-bromomethylbenzyl)-α/β-D-glucopyranoside

: 744-05-8,4198-49-6,7216-69-5,7216-73-1,21973-65-9,35438-39-2,58462-71-8,66101-74-4,66101-75-5,67145-39-5,67145-40-8,70399-66-5,70427-91-7,70428-28-3,80446-84-0,81131-44-4,84129-57-7,92282-08-1,93221-82-0,114580-08-4,114817-99-1,117064-58-1,117064-59-2,118493-11-1,118493-12-2,118493-13-3,127253-90-1,127641-09-2,130192-72-2,136890-91-0,145680-83-7,146683-50-3
methyl 4-O-β-D-glucopyranosyl-(1->4)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 45 percent / 15-crown-5; sodium hydride / CH₂Cl₂ / 2 h

2: 63 percent / trimethylsilyl trifluoromethanesulfonate; N-iodosuccinimide / toluene / 0.25 h / 20 °C

3: hydrogen; formic acid / palladium on carbon / methanol; ethyl acetate / 20 h

With N-iodo-succinimide; formic acid; 15-crown-5; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis;
DOI:10.1021/jo990132e