Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-L-furanosyl acetate from D-lactose

A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbrüggen conditions. Their structures were determined by 1D and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 microM.