SYNTHESIS AND ANTI-HIV ACTIVITY OF FURTHER EXAMPLES OF 1-[3-DEOXY-3-(N-HYDROXYAMINO)-BETA-D-THREO-(AND BETA-D-ERYTHRO)-PENTOFURANOSYL]THYMINE DERIVATIVES

Upon sodium cyanoborohydride reduction followed by de-O-silylation, th e O-methyloxime and N-benzylnitrone of 5'-TBDMS-3'-ketothymidine gave resolvable epimeric mixtures of 1-[2,3-dideoxy-3-(N-methoxyamino)-beta -D-treo- and beta-D-erythro-pentofuranosyl]thymine and N-benzyl-N-hydr dxyamino)-2,3-dideoxy-beta-D-threo- and beta-D-erythro-pentofuranosyl] thymine respectively. These compounds were inactive against HIV. On t he other hand, no)-5-O-TBDMS-beta-D-threo-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleos ide analogue 15, slightly more active against HIV in vitro than DDI.