ASYMMETRIC SYNTHESIS OF (2'R, 4'R) AND (2'S, 4'S)-1,3-DIOXOLANYL TRIAZOLE C-NUCLEOSIDES

Abstract In view of biological activities of both 1,3-dioxolanyl nucleosides and C -nucleosides, d - and l -1,3-dioxolanyl C -nucleosides have been synthesized as potential antiviral and/or anticancer agents. Asymmetric synthesis of four new optically pure d - and l -1,3-dioxolanyl triazole C -nucleosides has been accomplished via key intermediate 5a and 5b starting from d - and l -2,3-O-isopropylidene glyceraldehyde. The stereochemical assignments of synthesized compounds were unambiguously made based on NMR studies as well as X-ray crystallographic studies. The synthesized nucleosides have been evaluated against HIV and hepatitis B virus, however, no significant antiviral activity was observed.