phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside
CAS No.:874359-72-5
Molecular Formula:C₅₅H₄₈N₂O₁₂S
Molecular Weight:961.058
Hs Code.:

phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Synonyms:phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-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: 58.0%

: 1352630-94-4
phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside S-oxide

: 141342-83-8
phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside

: 874359-72-5
phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; In dichloromethane; at 20 ℃; for 0.75h; Inert atmosphere; Molecular sieve;

phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside S-oxide; In dichloromethane; at -78 - -40 ℃; for 4h; regioselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tet.2011.09.114

Reference yield:

: 100-39-0
benzyl bromide

: 874359-72-5
phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 20 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.75 h / -78 - 20 °C / Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 4 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

With 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2011.09.114

Reference yield:

: 208644-70-6
phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 874359-72-5
phenyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.75 h / -78 - 20 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 4 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

With 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1016/j.tet.2011.09.114