3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Base Information

Chemical Name:3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol
CAS No.:544686-89-7
Molecular Formula:C₄₉H₅₇N₃O₇Si
Molecular Weight:828.093
Hs Code.:

Synonyms:3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

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Chemical Property of 3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

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Technology Process of 3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

There total 6 articles about 3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-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: 56.0%

: 100-39-0
benzyl bromide

: (2R,3S,4R,5R,6S)-6-[(S)-1-Allyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-5-azido-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 544686-89-7
3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 30h; Inert atmosphere;
DOI:10.1021/ol2033652

Reference yield:

: 544686-87-5
(S)-(-)-1-allyl-3-tert-butyldiphenylsilyl-sn-glycerol

: 544686-89-7
3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 3 steps

1: TMSOTf / CH₂Cl₂ / 0.03 h / 20 °C

2: MeOH; NaOMe / pH 9

3: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

With methanol; sodium methylate; sodium hydride; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2004.11.070

Reference yield:

: 544686-88-6
3-O-allyl-2-O-(2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

: 544686-89-7
3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 2 steps

1: MeOH; NaOMe / pH 9

2: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

With methanol; sodium methylate; sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2004.11.070