Studies of Nucleosides and Nucleotides. LXXXIV. Purine Cyclonucleosides. XL. Cyclonucleosides derived from 5´-Deoxyadenosine

Abstract

5´-Deoxyadenosine (I) was brominated at the 8-position and converted to 8, 2´-(VI) and 8, 3´-S-cyclonucleosides (VII) via the 2´, 3´-dibutylstannylene compound by successive tosylation and heating with NaSH. When VI was treated with tert-butyl hypochlorite, an exo sulfoxide VIII was obtained. Desulfurization of VI and VII with Raney Ni gave 2´, 5´-(IX) and 3´, 5´-dideoxyadenosine (X), respectively. An 8, 2´-O-cyclonucleoside (XII) was also obtained from V by a standard procedure. Rearrangement of XII to a ribo-type epoxide (XIII) in the presence of 0.1 N NaOH was observed.