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

Mahesh Kasthuri (1) , Laurent Chaloin (2) , Christian Perigaud (1) , Suzanne Peyrottes (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 IRIM - Institut de Recherche en Infectiologie de Montpellier

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.

Domaines: Chimie organique

Mahesh Kasthuri, Laurent Chaloin, Christian Perigaud, Suzanne Peyrottes. Synthesis of (R)- and (S)-ßhydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA). Tetrahedron: Asymmetry, 2011, 22, pp.1505-1511. ⟨10.1016/j.tetasy.2011.08.010⟩. ⟨hal-00637860⟩