Enantiospecific synthesis of 3′-hetero-dideoxy nucleoside analogues as potential anti-HIV agents

Abstract

Two series of analogues of 2′,3′-dideoxy carbocyclic nucleosides, in which the 3′-carbon atom is replaced by either an oxygen or a sulfur atom, have been prepared enantiospecifically from diacetone-L-glucose and diacetone-D-glucose respectively. Within each series the guanosine, adenosine, uridine, cytidine and thymidine analogues were prepared, and their anti-HIV activity is discussed. X-Ray molecular structures of (2R,4R)-4-(6′-amino-9′H-purin-9′-yl)tetrahydrofuran-2-methanol and (3′R,5′R)-4-amino-1-{5′-[(benzyloxy)methyl]tetrahydro-3′-thienyl}pyrimidin-2(1H)-one have been determined.