N
6-Dimethyladenosine was derived to 8-brorro-2'-and 3'-TPS compounds by bromination with bromine-water at pH 4, followed by the reaction with NaH and TPS-Cl in DMF. From 2'-TPS compound 8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosyl-N
6-dimethyladenine (8, 2'-S-cyclonucleoside) and from 3'-TPS compound 8, 3'-anhydro-8-mercapto-9-β-D-xylofuranosyl-N
6-dimethyladenine (8, 3'-S-cyclonucleoside) were obtained. Structure of these cyclonucleosides were determined by ultraviolet (UV), nuclear magnetic resonance (NMR), circular dichroism (CD) and mass spectra. Desulfurization with Raney nickel gave 2'-deoxy and 3'-deoxy-N
6-dimethyladenosine, respectively. Treatment of 2'-and 3'-TPS compound with NaOAc in acetic acid-acetic anhydride mixture, followed by cyclization with ammonia-methanol gave 8, 2'-anhydro-8-oxy-9-β-D-arabinofuranosyl-(8, 2'-O-cyclonucleoside) and 8, 3'-anhydro-8-oxy-9-β-D-xylofuranosyl-N
6-dimethyladenine (8, 3'-O-cyclonucleoside), respectively. The structure of these cyclonucleoside was determined by UV, NMR, CD and mass spectra.
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