Synthesis of 2',3'-dideoxy-3'-fluorouridines with potential anti-HIV activity according to neural network calculations

Article abstract of DOI:10.1055/s-1994-25515

Methyl 2, 3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythropentofuranoside was condensed with trimethylsilylated 5-substituted uracils to give nucleosides using trimethylsilyl trifluoromethanesulfonate as catalyst. In the case of 5-nitrouracil an acyclic nucleoside believed to be an intermediate for the corresponding nucleoside was isolated. The 5-substituents were selected from neural network calculations on compounds with potential activity against HIV-1. All compounds from the condensation reactions were deacylated by treatment with sodium methoxide in methanol.