N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide

Base Information

• Chemical Name: N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide
• CAS No.: 1332725-08-2
• Molecular Formula: C₄₈H₆₂N₂O₁₂SSi
• Molecular Weight: 919.178
• Mol file: 1332725-08-2.mol

Synonyms:N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide

Chemical Property of N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide

There total 5 articles about N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide 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: 71.0%

methyl 6-amino-2,3,4-tri-O-benzyl-6-deoxy-6-N-(2-nitrobenzenesulfonyl)-α-D-mannopyranoside (1307860-15-6) + Ethyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (116455-00-6) → N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide (1332725-08-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; diastereoselective reaction; Inert atmosphere;

DOI:10.3762/bjoc.7.128

Reference yield:

ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside (52471-76-8,23339-15-3,56196-33-9,63526-95-4) → N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide (1332725-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Mitsunobu coupling reaction;

DOI:10.3762/bjoc.7.128

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-2-nitrobenzenesulfonamide (1332725-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: Mitsunobu coupling reaction;

DOI:10.3762/bjoc.7.128

upstream raw materials:

methyl 6-amino-2,3,4-tri-O-benzyl-6-deoxy-6-N-(2-nitrobenzenesulfonyl)-α-D-mannopyranoside

Ethyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside

2-Nitrobenzenesulfonyl chloride

Downstream raw materials:

N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 6-O-(tert-butyldimethylsilyl)-4-deoxy-α-D-mannopyranosid-4-yl)-2-nitrobenzenesulfonamide

N-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl)-N-(ethyl 4-deoxy-α-D-mannopyranosid-4-yl)-2-nitrobenzenesulfonamide