Synthesis of 2′-Deoxy-2′-β-fluoro-4′-azido-5-fluorouridine as a Potential Anti-HIV Agent

Abstract

2'-Deoxy-2'-β-fluoro-4'-azido-5-fluorouridine (1), a new pyrimidine nucleoside analog of Azvudine (FNC), is designed and synthesized. The synthesis of this nucleoside analog is achieved by bromination of 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-D-arabinofuranoside followed by the reaction with silylated 5-fluorouracil and further modification of the sugar moiety in a 7.6% overall yield over nine steps. Compound 1 exhibited good antiviral activity against HIV-1 infection in HEK293T cells.