Studies of Nucleosides and Nucleotides. LXXXV. Purine Cyclonucleosides. (35). Synthesis of Purine Nucleosides having 2'-Azido and 2'-Amino Functions by Cleavage of Purine Cyclonucleosides

Abstract

8, 2'-O-Cycloadenosine (I) was attacked by azide ion to give 8-oxy-2'-azide compound (II). The 8-oxy function of II was eliminated by derivatization to inosine (IV), acetylation to give V, chlorination with POCl₃ to VI, treatment with sodium methylmercaptide to give 6, 8-bis (methylmercapto) compound (VII), reaction with dimethylamine to give VIII and Raney nickel dethiolation to give N⁶-dimethyl-2'-amino-2'-deoxyadenosine (IX). The compound VI was thiolated into X and treated with hydrogen peroxide to give 3', 5'-di-O-acetyl-2'-azido-2'-deoxyinosine (XI), which was deacetylated to 2'-azido-2'-deoxyinosine (XII). The compound XI was chlorinated and treated with ammonia to give 2'-azido-2'-deoxyadenosine.