allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Base Information

Chemical Name:allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside
CAS No.:1616860-53-7
Molecular Formula:C₅₂H₅₄Cl₃NO₁₁
Molecular Weight:975.36
Hs Code.:

Synonyms:allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Chemical Property of allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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Technology Process of allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

There total 4 articles about allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-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: 72.0%

: 1616860-52-6
allyl (2,3-di-O-benzoyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 100-39-0
benzyl bromide

: 1616860-53-7
allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: allyl (2,3-di-O-benzoyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside; With 15-crown-5; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 15h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; for 20h; regioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201400269

Reference yield:

: 1616860-51-5
allyl 4,6-O-di-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 1616860-53-7
allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C

2.1: 15-crown-5; sodium hydroxide / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

2.2: 20 h / Inert atmosphere

With 15-crown-5; trimethylsilyl trifluoromethanesulfonate; sodium hydroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1002/adsc.201400269

Reference yield:

: 1061181-49-4
allyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 1616860-53-7
allyl (2,3-di-O-benzyl-4,6-O-benzylidine-β-D-glucopyranosyl)-(1→3)-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 15-crown-5; sodium hydroxide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 8 h / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C

3.1: 15-crown-5; sodium hydroxide / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

3.2: 20 h / Inert atmosphere

With 15-crown-5; trimethylsilyl trifluoromethanesulfonate; sodium hydroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1002/adsc.201400269