Studies of Nucleosides and Nucleotides. LI. Purine Cyclonucleosides. (16). Synthesis of Cyclonucleosides derived from N^6-Dimethyladenosine
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概要
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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.
- 公益社団法人日本薬学会の論文
- 1971-12-25
著者
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森沢 弘和
Faculty of Pharmaceutical Sciences, Osaka University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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森沢 弘和
Faculty Of Pharmaceutical Sciences Osaka University
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