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4(S)-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2(S)-ylmethyl phosphonic acid, a 5′-Cphosphonate analog of the potent anti-HIV compound S,S-IsoddA, was synthesized in order to bypass the critical initial intracellular phosphorylation. Key phases in this multistep synthesis were the Arbuzov reaction of the 5-iodofuranose with triethylphosphite and the Mitsunobu/ coupling reaction of the phosphonate with adenine. The structure of the final product was confirmed by HRMS and multinuclear NMR data.

Synthesis of the 5'-C-phosphonate of 4(S)-(6-amino-9H-purin-9-yl) tetrahydro-2(S)-furanmethanol [S,S-IsoddA]