Synthesis of 8,2'-Methanoguanosine and 9-(α-D-Arabinofuranosyl)-8,2'-methanoguanine (Nucleosides and Nucleotides. LXVII.)

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概要

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• Guanosine fixed in the high-anti conformation by means of an 8,2'-methylene bridge was prepared. N^2-Acetyl-O^6-ethylguanosine (2) was converted to the 3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl) derivative (3). Oxidation of 3 to the 2'-keto derivative (4) and successive coupling with methylenetriphenylphosphorane gave the 2'-methylidene derivative (5) and its α-anomer. The 2'-methylidene function of 5 was hydroxylated, and the 2'-hydroxymethyl group was modified to give the phenylthiomethyl derivative (6). Photocyclization of 6 followed by deprotection of the sugar and base protecting groups furnished 8,2'-methanoguanosine (12). The alpha anomer of 12 was likewise prepared. The circular dichroism spectra of 12,its α-anomer, and related compounds were measured.

• 公益社団法人日本薬学会の論文
• 1986-05-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 松田 彰

  Faculty Of Pharmaceutical Sciences 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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