• DOI:10.1080/15257770.2012.696759
• Corpus ID: 205855028

Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

@article{Manta2012StereocontrolledFS,
  title={Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides},
  author={Stella Manta and Vanessa Parmenopoulou and Christos Kiritsis and Athina Dimopoulou and Nikolaos Kollatos and Ioannis Papasotiriou and Jan Balzarini and Dimitri Komiotis},
  journal={Nucleosides, Nucleotides \& Nucleic Acids},
  year={2012},
  volume={31},
  pages={522 - 535}
}

• S. Manta, V. Parmenopoulou, +5 authors D. Komiotis
• Published 1 July 2012
• Chemistry
• Nucleosides, Nucleotides & Nucleic Acids

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.