(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Base Information

Chemical Name:(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate
CAS No.:934349-45-8
Molecular Formula:C₃₇H₃₉N₃O₇
Molecular Weight:637.733
Hs Code.:

Synonyms:(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Chemical Property of (2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Technology Process of (2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

There total 5 articles about (2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 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: 81.0%

: 934349-43-6
trifluoromethanesulfonyloxy-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

: 934349-45-8
(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: With sodium azide; 15-crown-5; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1055/s-2007-968002

Reference yield:

: 883143-12-2
(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

: 934349-45-8
(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tributyltin hydride; trimethylsilyltrifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 100 percent / trifluoroacetic acid / tetrahydrofuran; CH₂Cl₂ / 2 h

2.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 81 percent / sodium azide; 15-crown-5 / CH₂Cl₂ / 24 h / 20 °C

With pyridine; sodium azide; 15-crown-5; trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane;
DOI:10.1055/s-2007-968002

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 934349-45-8
(2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / LiHMDS / tetrahydrofuran / 2 h / -78 - 20 °C

2.1: tributyltin hydride; trimethylsilyltrifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 100 percent / trifluoroacetic acid / tetrahydrofuran; CH₂Cl₂ / 2 h

3.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: 81 percent / sodium azide; 15-crown-5 / CH₂Cl₂ / 24 h / 20 °C

With pyridine; sodium azide; 15-crown-5; trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2007-968002