Synthesis of 5′-Triphosphate Mimics (P3Ms) of 3′-Azido-3′,5′-Dideoxythymidine and 3′,5′-Dideoxy-5′-Difluoromethylenethymidine as HIV-1 Reverse Transcriptase Inhibitors.

3'-Azido-3',5'-dideoxythymidine 5'-phosphonate and 3',5'-dideoxy-5'-difluoromethylenethymidine 5'-phosphonate were prepared by multistep syntheses. The nucleoside 5'-phosphonates were converted to their triphosphates and triphosphate mimics (P3Ms) containing ß,?-difluoromethylene, ß,?-dichloromethylene, or ß,?-imodo by condensation with pyrophosphate or pyrophosphate mimics, respectively. Inhibition of HIV-1 reverse transcriptase by the nucleoside P3Ms is briefly discussed. [ABSTRACT FROM AUTHOR]