Synthesis of 8-Alkyladenosines, 8,2'-Anhydro-8-hydroxymethyl-9-(β-D-arabinofuranosyl) adenine and Related Compounds (Nucleosides and Nucleotides. LVIII)

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概要

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• Synthesis of 8-alkyladenosines and related nucleosides is described. Treatment of 5'-O-acetyl-2', 3'-O-isopropylidene-8-methylsulfonyladenosine with ethyl sodioacetoacetate gave the 8-ethoxy-carbonylmethyl derivative (1). Hydrolytic decarboxylation of 1 followed by deacetonation afforded 8-methyladenosine (2) in high yield. Alkylation of 1 with methyl or ethyl iodide followed by hydrolytic decarboxylation afforded 8-ethyl- and 8-propyladenosines, respectively. Attempts at dimethylation of the 8-methylene group of 1 resulted in the formation of the N^6-dimethyladenosine derivative. Selective dimethylation of the amino groups of 2'-deoxyadenosine and 2'-deoxycytidine has been accomplished by using a combination of methyl iodide and sodium hydride without methylation of the sugar hydroxyl groups of these nucleosides. 8,2'-Anhydro-9-β-D-arabinofuranosyl-8-hydroxymethyladenine was prepared from a 8-cyanoadenosine derivative by the procedure involving anhydro-bond formation by base treatment of 8-hydroxymethyl-2'-Otosyladenosine. The circular dichroism spectral characteristics of 8-alkyladenosines are discussed.

• 公益社団法人日本薬学会の論文
• 1985-08-25

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

• 野本 裕二

  Pharmaceutical Research Laboratories, Fuji, Kyowa Hakko Kogyo Co., Ltd.,

• 上田 亨

  北海道大学薬学部

• 野本 裕二

  Pharmaceutical Research Laboratories Fuji Kyowa Hakko Kogyo Co. Ltd.

• 野本 裕二

  Faculty of Pharmaceutical Sciences, Hokkaido University

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