p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
CAS No.:1380218-20-1
Molecular Formula:C₅₄H₅₆N₆O₈S
Molecular Weight:949.14
Hs Code.:

Synonyms:p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

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Chemical Property of p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

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Technology Process of p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

There total 9 articles about p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-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: 77.0%

: 671809-99-7
p-tolyl 2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

: 2-azido-2-deoxy-3,4,6-tri-O-benzyl-D-glucopyranosyl diphenyl phosphate

: 1380218-20-1
p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; propiononitrile; at -70 - -65 ℃; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1002/ejoc.201200173

Reference yield:

: 4-methylphenyl 2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside

: 1380218-20-1
p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / water; acetone / 1 h / 0 - 20 °C

2.2: 0 °C / Inert atmosphere

3.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile; propiononitrile / -70 - -65 °C / Molecular sieve; Inert atmosphere

With N-Bromosuccinimide; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; propiononitrile;
DOI:10.1002/ejoc.201200173

Reference yield:

: 929040-77-7,501088-45-5
4-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside

: 1380218-20-1
p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanol; sodium / dichloromethane / 3 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

3.1: N-Bromosuccinimide / water; acetone / 1 h / 0 - 20 °C

3.2: 0 °C / Inert atmosphere

4.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile; propiononitrile / -70 - -65 °C / Molecular sieve; Inert atmosphere

With methanol; N-Bromosuccinimide; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; sodium; sodium hydride; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; propiononitrile;
DOI:10.1002/ejoc.201200173