Synthesis and anti-hiv activity of further examples of l-[3-deoxy-3-(n-hydroxyamino)-β-d-threo- (and β-d-erythro)-pentofuranosyl]thymine derivatives1

Jean M.J. Tronchet, Martina Zsály, Olivier Lassout, Francoise Barbalat-Rey, Istvan Komaromi

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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.

Original languageEnglish
Pages (from-to)575-588
Number of pages14
JournalJournal of Carbohydrate Chemistry
Issue number4-5
Publication statusPublished - May 1 1995


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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