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Synthesis 1994; 1994(5): 516-520
DOI: 10.1055/s-1994-25515
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Synthesis of 2′,3′-Dideoxy-3′-fluorouridines with Potential Anti-HIV Activity According to Neural Network Calculations

Mamdouh A. Sofan* , Ahmed E.-S. Abdel-Megied, Morten B. Pedersen, Erik B. Pedersen, Claus Nielsen
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publikationsdatum:
17. September 2002 (online)

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Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 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.