methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
CAS No.:1380218-24-5
Molecular Formula:C₅₂H₅₃N₃O₁₀
Molecular Weight:880.007
Hs Code.:

Synonyms:methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Chemical Property of methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Technology Process of methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

There total 6 articles about methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-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: 80.0%

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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

: 1380218-24-5
methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; p-tolyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-galactopyranside; In dichloromethane; acetonitrile; propiononitrile; at -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; propiononitrile; at -60 ℃; for 4h; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1002/ejoc.201200173

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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

: 1380218-24-5
methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 1380218-23-4
methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-α-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: p-tolyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-galactopyranside; With 4-morpholinecarboxaldehyde; In dichloromethane; for 0.333333h; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; In dichloromethane; at 0 ℃; for 17h; Overall yield = 83 %; Overall yield = 78.6 mg;
DOI:10.1021/ol402519c

Reference yield:

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

: 1380218-24-5
methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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 / 0.5 h / -60 °C / Molecular sieve; Inert atmosphere

2.2: 4 h / -60 °C / Molecular sieve; Inert atmosphere

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