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Nucleosides Nucleotides Nucleic Acids. 2012;31(7):522-35. doi: 10.1080/15257770.2012.696759.

Stereocontrolled facile synthesis and biological evaluation of (3'S) and (3'R)-3'-amino (and Azido)-3'-deoxy pyranonucleosides.

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1
Laboratory of Bio-Organic Chemistry Department of Biochemistry and Biotechnology, University of Thessaly, Larissa, Greece.

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.

PMID:
22849646
DOI:
10.1080/15257770.2012.696759
[Indexed for MEDLINE]

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