38191-71-8

Basic information

• Product Name: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• Synonyms: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• CAS NO: 38191-71-8
• Molecular Weight: 342.306
• Mol File: 38191-71-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside(38191-71-8)
• EPA Substance Registry System: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside(38191-71-8)

Safety Data

• Hazardous Substances Data: 38191-71-8(Hazardous Substances Data)

Upstream product

• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 72-87-7 N-acetyl-D-mannosamine 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-mannopyrano)-[2,1:4',5']-2-oxazoline 
• 570412-04-3 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 
• 100-02-7 4-nitro-phenol 
• 570412-09-8 4-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside 

Downstream Products

• 148706-78-9 p-nitrophenyl-2-acetamido-3,4-benzoyl-6-O-trityl-2-deoxy-α-D-mannopyranoside 
• 148706-80-3 p-nitrophenyl-2-acetamido-3,4-di-O-benzoyl-2-deoxy-α-D-mannopyranoside 

Relevant articles and documents

Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D- mannopyranosides from ManNAc-oxazoline

The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.

Synthesis of 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside

The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound 8 was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.