Synthesis and antiviral activity of novel phenyl branched apiosyl nucleosides

Novel phenyl branched apiosyl nucleosides were synthesized in this study. The introduction of phenyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The natural bases (cytosine and adenine) were efficiently coupled with an apiosyl sugar by classical glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV.