Collect. Czech. Chem. Commun.
2003, 68, 801-811
https://doi.org/10.1135/cccc20030801
Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside
Pavel Krista, Marek Kuzmab, István F. Pelyvásc, Pavla Simerskáa and Vladimír Křena,*
a Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
b Laboratory of Molecular Structure Characterization, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
c Research Group of Antibiotics, Hungarian Academy of Sciences, University of Debrecen, P.O. Box 70, H-4010 Debrecen, Hungary
Abstract
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.
Keywords: N-Acetylmannosamine; β-Mannopyranosides; Aminosugars; Glycosylation; Glycosides; Glycosyl donors; Immunology; Immunostimulants.
References: 23 live references.
