Synthesis of 2'-Deoxy-8,2'-ethanoadenosine and 3'-Deoxy-8,3'-ethanoadenosine : Nucleosides and Nucleotides. LXIV

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概要

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• 2'-Deoxy-8,2'-ethanoadenosine and its 3'-isomer were synthesized from 2'- and 3'-keto-adenosine derivatives. Treatment of 3', 5'-O-(tetraisopropyldisiloxane-1,3-dilyl)-2'-ketoadenosine with ethoxycarbonylmethylenetriphenylphosphorane gave the 2'-ethoxycarbonylmethylene derivative, which was reduced to the 2'-hydroxyethyl derivative. This compound was converted to the 2'-iodoethyl-N^6,N^6-dibenzoyladenosine, which was cyclized by treatment with tri-n-butyltin hybride, then deprotected to furnish 2'-deoxy-8,2'-ethanoadenosine. Photocyclization of a 2'-phenylthioethyl derivative also gave the ethano-cycloadenosine. 3'-Deoxy-8,3'-ethanoadenosine was prepared from 2', 5'-di-O-(tert-butyldimethylsilyl)-3'-ketoadenosine via 2', 5'-di-O-acetyl-3'-deoxy-3'-phenylthioethyladenosine by photocyclization. The circular dichroism spectral features of these cycloadenosines are presented.

• 公益社団法人日本薬学会の論文
• 1986-01-25

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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