Title: Stereocontrolled facile synthesis and biological evaluation of (3'S) and (3'R)-3'-amino (and azido)-3'-deoxy pyranonucleosides
Authors: Manta, Stella ×
Parmenopoulou, Vanessa
Kiritsis, Christos
Dimopoulou, Athina
Kollatos, Nikolaos
Papasotiriou, Ioannis
Balzarini, Jan
Komiotis, Dimitri #
Issue Date: Jul-2012
Publisher: Marcel Dekker
Series Title: Nucleosides, Nucleotides & Nucleic Acids vol:31 issue:7 pages:522-535
Abstract: This article describes the synthesis of (3 'S) and (3 'R)-3 '-amino-3 '-deoxy pyranonucleosides and their precursors (3 'S) and (3 'R)-3 '-azido-3 '-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-α-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3 '-amino-3 '-deoxy-β-D-glucopyranonucleosides. The desired 1-(3 '-amino-3 '-deoxy-β-D-allopyranosyl)5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.
ISSN: 1525-7770
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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