SYNTHESIS AND ANTI-HIV ACTIVITY OF NEW 3 '-O-PHOSPHONOMETHYL NUCLEOSIDES

Authors：Cesnek, Michal^*; Herdewijn, Piet

Source：Heterocycles, 2010, 82(1): 663-687.

DOI：10.3987/COM-10-S(E)42

• Phosphonate
• HIV
• PMDTT
• PMDTA
• Bestmann Modification

The synthesis of 4'(S)-ethynyl-2'-deoxythreosyl and beta-D-galactofuranose nucleosides starting from D-galactose is described. The nucleobase is introduced using Vorbruggen glycosylation. The 4'(S)-ethynyl derivatives are obtained by selective oxidation of vicinal diol to the aldehyde and subsequent Bestmann modification of Seyferth-Gilbert homologation. All compounds were evaluated for activity against HIV (MT4 cells), RSV (Hep2 cells) and HCV (HCV replicon cells), however, none of these compounds demonstrate biological activity.

• Institution
  河北医科大学