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Synthesis of (R)- and (S)-ßhydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
Journal article   Peer reviewed

Synthesis of (R)- and (S)-ßhydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

Mahesh Kasthuri, Laurent Chaloin, Christian Perigaud and Suzanne Peyrottes
Tetrahedron: Asymmetry, Vol.22, pp.1505-1511
2011
PMCID: PMC7125833

Abstract

A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside ß-ketophosphonate, readly available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-ß-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies.
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