methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

Base Information

Chemical Name:methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside
CAS No.:710965-66-5
Molecular Formula:C₃₁H₃₅N₃O₇
Molecular Weight:561.635
Hs Code.:

Synonyms:methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

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Chemical Property of methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

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Technology Process of methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

There total 4 articles about methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-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: 96.0%

: 710965-65-4
(S)-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-iodo-acetic acid methyl ester

: 710965-66-5
methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 28 ℃; for 24h;
DOI:10.1021/ol049467v

Reference yield: 85.0%

: 946512-99-8
methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(methoxycarbonyl)methyl]-β-D-glucopyranoside

: 710965-66-5
methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

Guidance literature:: methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(methoxycarbonyl)methyl]-β-D-glucopyranoside; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; at -78 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1039/b918893m

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 710965-66-5
methyl (7R)-3,4,6-tri-O-benzyl-2-deoxy-2C-[(azido)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 59 percent / Rh₂(OAc)4 / CH₂Cl₂ / 1.5 h / 20 °C

2: 75 percent / N-iodosuccinimide / 8 h / 28 °C

3: 96 percent / sodium azide / dimethylformamide / 24 h / 28 °C

With dirhodium tetraacetate; N-iodo-succinimide; sodium azide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol049467v