Diastereoselective synthesis of the potent antiviral agent (-)-2'-deoxy-3'-thiacytidine and its enatiomer

A novel diastereoselective N-glycosylation reaction can be used to synthesize the clinically important nucleoside, (-)-2'-deoxy-3'-thiacytidine (3TC) and its (+) enatiomer. Chromatographic separation of isomers is not necessary and the starting materials for the reaction are inexpensive.This procedure has greater yields than the enzymatic resolution of the anti-HIV dideoxy nucleoside analog BCH-189' as well as producing the potent antiviral agent (+) BCH-189 more efficiently than methods using naturally occurring sugars.