benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside

Base Information

• Chemical Name: benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside
• CAS No.: 155688-57-6
• Molecular Formula: C₂₂H₃₃NO₉S
• Molecular Weight: 487.571

Synonyms:benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside

Chemical Property of benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside

Chemical Property:

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Technology Process of benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside

There total 3 articles about benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside 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: 87.0%

methanesulfonyl chloride (124-63-0) + benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-D-mannopyranoside (155688-56-5) → benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside (155688-57-6)

Guidance literature:

With dmap; In pyridine; dichloromethane; for 20h;

DOI:10.1016/S0040-4020(01)80815-2

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside (155688-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / tetrahydrofuran / 16.5 h / Ambient temperature

2: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 20 h

With dmap; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)80815-2

Reference yield:

benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside (95066-29-8) → benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-6-O-methane-sulfonyl-D-mannopyranoside (155688-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / tetrahydrofuran / 16.5 h / Ambient temperature

2: 87 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 20 h

With dmap; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)80815-2

upstream raw materials:

methanesulfonyl chloride

benzyl 4-(N-(tert-butoxycarbonyl)amino)-4-deoxy-2,3-O-isopropylidene-D-mannopyranoside

di-tert-butyl dicarbonate

benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

benzoyl 6-azido-4-(N-(tert-butoxycarbonyl)amino)-4,6-dideoxy-2,3-O-isopropylidene-D-mannopyranoside

benzyl 6-azido-4-(N-(tert-butoxycarbonyl)amino)-4,6-dideoxy-2,3-O-isopropylidene-D-mannopyranoside

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