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Synthesis of unnatural 3′-phospha-2′-deoxyfuranose nucleoside analogues.
Journal article   Peer reviewed

Synthesis of unnatural 3′-phospha-2′-deoxyfuranose nucleoside analogues.

Bénédicte Dayde, Claire Pierra, Gilles Gosselin, Dominique Surleraux, Amadou Tidjani Ilagouma, Jean-Noël Volle, David Virieux and Jean-Luc Pirat
Tetrahedron Letters, Vol.55(46)
12/11/2014

Abstract

Deoxy nucleosides analogues Pudovik reaction P-alkylation reaction Radical deiodination
This Letter describes the synthesis of racemic analogues of unnatural 2′-deoxy nucleoside with a phosphorus atom replacing the carbon atom in the 3′-position. A seven-step sequence was developed in racemic series to afford unnatural 3′-phospha-2′-deoxyfuranose nucleosides. The phospha nucleoside analogues were tested against HCV, but did not show any antiviral activity at a 10 μM maximum concentration used for the inhibition assays of analogues 2-T, 2-C and 4-Tα.
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