著者

松田 彰 野本 裕二 上田 亨

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.27, no.1, pp.183-192, 1979-01-25 (Released:2008-03-31)

被引用文献数

16 31

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A facile displacement of a methylsulfonyl group in adenosines with cyanide ion is described. Treatment of protected 8-methylsulfonyladenosines with sodium cyanide in dimethylformamide gave the 8-cyanoadenosines. The conversion of the cyano group to the methyl imidate, methoxycarbonyl, carbamoyl, and carboxylic acid, respectively, was achieved. Similar reaction was carried out with 2-methylsulfonyladenosines to give the 2-cyanoadenosines and their derivatives. The nuclear magnetic resonance (NMR) and circular dichroism (CD) spectra of these 2-and 8-substituted adenosines are given. The 8-substituted adenosines possess syn-conformations while the 2-substituted derivatives prefer to possess anti-conformations, as confirmed by the CD and NMR spectra.