ENANTIOSPECIFIC SYNTHESIS OF 3'-HETERO-DIDEOXY NUCLEOSIDE ANALOGS AS POTENTIAL ANTI-HIV AGENTS

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.