SYNTHESIS OF 3'-N-SUBSTITUTED 3'-AMINO-3'-DEOXYTHYMIDINE DERIVATIVES

A series of 3'-N-substituted 3'-amino-3'-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-O-mesyl-5-O-trityl-beta-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3'-amino-5'-O-trityl-3'-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3'-amino-3'-deoxythymidine from 3'-azido-5'-O-trityl-3'-deoxythymidine using sodium borohydride was also described.