(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Base Information

Chemical Name:(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol
CAS No.:1574348-17-6
Molecular Formula:C₃₉H₅₃N₃O₆Si
Molecular Weight:687.952
Hs Code.:

Synonyms:(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

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Chemical Property of (1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

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Technology Process of (1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

There total 5 articles about (1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol 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%

: 1574348-16-5
(1R,2R)-1-O-(2-azido-2-deoxy-β-D-glucopyranosyl)-2-O-(tertbutyldimethylsilyl)cyclohexanediol

: 100-39-0
benzyl bromide

: 1574348-17-6
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: (1R,2R)-1-O-(2-azido-2-deoxy-β-D-glucopyranosyl)-2-O-(tertbutyldimethylsilyl)cyclohexanediol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c3ob42164c

Reference yield:

: 1574347-73-1
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)cyclohexanediol

: 1574348-17-6
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium methylate; methanol / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; sodium methylate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob42164c

Reference yield:

: 145840-43-3
3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate

: 1574348-17-6
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium methylate; methanol / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

4.2: 24 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob42164c