3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Base Information

Chemical Name:3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol
CAS No.:1383450-02-9
Molecular Formula:C₃₃H₃₉N₃O₇
Molecular Weight:589.689
Hs Code.:

Synonyms:3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

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Chemical Property of 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

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Technology Process of 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

There total 18 articles about 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol 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:

: 22323-82-6,36543-79-0
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

: p-tolyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

: 1192755-03-5
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

: 1383450-02-9
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: p-tolyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; In diethyl ether; at 20 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 20 ℃; for 72h; optical yield given as %de; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.carres.2012.04.005

Reference yield:

: C₁₂H₂₁N₃O₇

: 100-39-0
benzyl bromide

: 1383450-02-9
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1039/c4ob00721b

Reference yield:

: 191668-79-8
O-(2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranosyl)trichloroacetimidate

: 1383450-02-9
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 4 h / -15 - 0 °C / Molecular sieve

2: methanol; sodium methylate

3: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

With methanol; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c4ob00721b