methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

Base Information

Chemical Name:methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate
CAS No.:1461641-33-7
Molecular Formula:C₄₂H₄₅N₃O₁₁
Molecular Weight:767.833
Hs Code.:

Synonyms:methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

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Chemical Property of methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

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Technology Process of methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

There total 3 articles about methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate 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: 89.0%

: 29398-07-0
1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester

: 1333393-48-8
p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

: 1461641-33-7
methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

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

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

1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester; In dichloromethane; at -10 ℃; for 24h;
DOI:10.1021/ol402519c

Reference yield:

: 29398-07-0
1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester

: 1333393-48-8
p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

: 1461641-33-7
methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

: 1461641-35-9
methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

Guidance literature:: 1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester; p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside; In dichloromethane; acetonitrile; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -60 ℃; for 1h; Overall yield = 85 %; Overall yield = 162 mg; Inert atmosphere;
DOI:10.1021/ol402519c

Reference yield:

: 17791-36-5
methyl 2,3-di-O-benzyl-α-D-glucopyranoside

: 1461641-33-7
methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

: 1461641-35-9
methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; sodium hypochlorite / dichloromethane; water / 1 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

3.1: dichloromethane; acetonitrile / 0.5 h / Molecular sieve; Inert atmosphere

3.2: 1 h / -60 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol402519c