570412-06-5

Upstream product

• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 
• 87236-45-1 4-nitrophenyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 53872-80-3 bromure de tri-O-acetyl-3,4,6-α-D-glucopyranosyle 
• 845271-56-9 4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 570412-05-4 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside 

Downstream Products

• 570412-11-2 4-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-mannopyranoside 
• 50645-66-4 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside 

Relevant academic research and scientific papers

A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- and β-d-mannopyranosides were prepared from methyl 4,6-O-benzylidene-α-d- glucopyranoside and 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-α-d- and -β-d-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-α-d- mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-β-d-mannopyranoside in 20% and 44% overall yields, respectively.

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.