Synthesis of 8,2'-Methano- and 8,2'-Ethanoadenosines(Nucleosides and Nucleotides. LXV)

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概要

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• Treatment of 3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-ketoadenosine (1) with methylenetriphenylphosphorane gave the 2'-methylene derivative (2). Hydroxylation of 1 with OsO_4 gave the 2'-hydroxymethyladenosine (4), which was then converted to the 2'-phenylthiomethyl derivative (5). Photocyclization followed by deprotection of the product furnished 8,2'-methanoadenosine (7), and adenosine fixed in a high-anti conformation. Oxidation of a 2'-hydroxyethylideneadenosine with OsO_4 gave the 2'-dihydroxyethyladenosine (10), which was also converted to the 2'-(2-phenylthioethyl) derivative (11). The photocyclization of 11 and successive elimination of the hydroxyl group gave the 8,2'-ethenoadenosine (13). Catalytic hydrogenation and deprotection of 13 afforded 8,2'-ethanoadenosine (15). The circular dichroism spectral features of C-cycloadenosine are discussed.

• 公益社団法人日本薬学会の論文
• 1986-04-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 上田 亨

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 碓井 博幸

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 上田 亨

  北海道大学薬学部

• 碓井 博幸

  Daiichi Pharmaceutical Co., Ltd.,

• 碓井 博幸

  Daiichi Pharmaceutical Co. Ltd.

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