6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

Base Information

Chemical Name:6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside
CAS No.:1380218-26-7
Molecular Formula:C₃₀H₃₄ClN₃O₅
Molecular Weight:552.07
Hs Code.:

Synonyms:6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

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Chemical Property of 6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

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Technology Process of 6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

There total 5 articles about 6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside 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: 80.0%

: 2009-83-8
6-chloro-1-hexanol

: 1380218-33-6
p-tolyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-galactopyranside

: 1380218-26-7
6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

Guidance literature:: 6-chloro-1-hexanol; p-tolyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-galactopyranside; In dichloromethane; acetonitrile; propiononitrile; at -70 ℃; for 1h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; propiononitrile; at -70 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1002/ejoc.201200173

Reference yield:

: 125760-23-8
4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

: 1380218-26-7
6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

2.1: dichloromethane; acetonitrile; propiononitrile / 1 h / -70 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -70 °C / Molecular sieve; Inert atmosphere

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; propiononitrile; mineral oil;
DOI:10.1002/ejoc.201200173

Reference yield:

: p-tolyl 2-deoxy-2-azido-1-thio-α/β-D-galactopyranoside

: 1380218-26-7
6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

3.1: dichloromethane; acetonitrile; propiononitrile / 1 h / -70 °C / Molecular sieve; Inert atmosphere

3.2: 2 h / -70 °C / Molecular sieve; Inert atmosphere

With sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; propiononitrile; mineral oil;
DOI:10.1002/ejoc.201200173