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

Base Information

• Chemical Name: methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate
• CAS No.: 1461641-29-1
• Molecular Formula: C₄₉H₅₃N₃O₁₁
• Molecular Weight: 859.973

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

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

Chemical Property:

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

There total 8 articles about methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(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:

1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester (29398-07-0) + 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside → methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-29-1) + methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-30-4)

Guidance literature:

1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester; 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside; In dichloromethane; acetonitrile; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -60 ℃; for 5h; Overall yield = 74 %; Overall yield = 158 mg; Inert atmosphere;

DOI:10.1021/ol402519c

Reference yield:

methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-29-1) + methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-30-4)

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: 5 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

Reference yield:

methyl 2,3-di-O-benzyl-α-D-glucopyranosiduronic acid (50711-26-7) → methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-29-1) + methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-1-O-methyl-α-D-glucopyranosyluronate (1461641-30-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: 5 h / -60 °C / Inert atmosphere

With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol402519c

upstream raw materials:

methyl 2,3-di-O-benzyl-α-D-glucopyranoside

1-O-methyl-2,3-di-O-benzyl-α-D-glucopyranuronic acid methyl ester

methyl 2,3-di-O-benzyl-α-D-glucopyranosiduronic acid

4’-methyl phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside

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