SYNTHESES OF NOVEL HYDROXYLAMINE CARBANUCLEOSIDES

Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleoside s have been synthesized as isosteric 4'-hydroxymethyl analogs to carbo vir, ddA, and aristeromycin. The key steps in the syntheses involved a n enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylati on, overcoming the syn-directing effect seen in osmium tetroxide-media ted dihydroxylations. Hydroxylamino-propane analogs were also synthesi zed through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All right s reserved.