The chemistry of 2′,3′-seconucleosides IV. Synthesis and reactions of 3′-azido-2′,3′-dideoxy-2′,3′- secothymidine and related analogues

Article abstract of DOI:10.1016/S0040-4020(01)85449-1

The synthesis of a series of 2,3-seconucleoside analogues related to nucleosides previously shown to possess anti-HIV activity is described. Using strategies to distinguish between the three primary hydroxyl groups of a 2,3-seconucleoside, 3-azido-2,3-dideoxy-2,3-secothymidine and 2,3-dideoxy-2,3-secothymidine have been prepared. These compounds, several of the intermediates in their synthesis, as well as O²2-anhydro-3-azido-3-deoxy-2,3-secothymidine and several 2,3-secouridine analogues have been tested for their ability to prevent infection of cells by HIV. None showed any significant toxicity or antiviral activity.