Upon sodium cyanoborohydride reduction followed by de-O-silylation, the O-methyloxime and N-benzylnitrone of 5-TBDMS-3’-ketothymidine gave resolvable epimeric mixtures of l-[2, 3-dideoxy-3-(N-methoxyamino)-β-D-threo-and β-D-erythro-pentofuranosyl]thymine and l-[3-(N-benzyl-N-hydroxyamino)-2, 3-dideoxy-β-D-threo-and β-D-erythro-pentofuranosyl]thymine respectively. These compounds were inactive against HIV. On the other hand, l-[2, 3-dideoxy-3-(N-hydroxyamino)-5-0-TBDMS-β-D-tftra)-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleoside analogue 15, slightly more active against HIV in vitro than DDI.
ASJC Scopus subject areas
- Organic Chemistry