Studies of Nucleosides and Nucleotides. LXXX. Purine Cyclonucleosides. (38). Synthesis of 6-Substituted Purine 2'-Azido-and 2'-Amino-2'-deoxyribofuranosides

Abstract

Starting from 2'-azido-2'-deoxyadenosine (1), sugar-acetylated 6-chloro compound (5) was synthesized by successive deamination, acetylation and chlorination. Using the compound 5 as intermediate 6-monomethylamino-, dimethylamino-, mercapto- and methylthio 2'-azido nucleosides (6, 8, 11 and 12) were obtained. Palladium-catalyzed hydrogenation of compound 6 and 8 afforded 2'-amino nucleosides (7 and 9) respectively.