A systematic synthesis was undertaken of 2', 3'-dideoxyadenosine analogues with either an azido, fluorine, or hydroxyl group substituted in the “up” or “downn position of C-2 or C-3 of the sugar moiety. The compounds were evaluated against the cytopathogenicity of human immunodeficiency virus (HIV) for MT-4 cells. The four azido derivatives 6, 7, 8, and 9 were synthesized by a nucleophilic displacement reaction with lithium azide on the mesylates 3, ...