Synthesis of 5'-Hydroxyalkyl-5'-deoxy-8,5'(R and S)-cycloadenosines (Nucleosides and Nucleotides. XXXI)

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概要

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• Treatment of 2', 3'-O-isopropylidene-5'-oxo-8,5'-cycloadenosine with dimethyloxosulfonium methylide followed by hydrogenation afforded the diastereomeric pairs of 5'-methyl-5'-deoxy-8,5'-cycloadenosine and 5'-hydroxymethyl-5'-deoxy-8,5'-cycloadenosine. The configurations at the 5'-positions of these 8,5'-cycloadenosines were determined by nuclear magnetic resonance (NMR) measurements. The Wittig reactions of the 5'-oxo-8,5'-cycloadenosine with methoxymethylenetriphenylphosphorane, methylthiomethylenetriphenylphosphorane, and ethyl (dimethylsulfuranylidene) acetate afforded the corresponding 5'-substituted derivatives. The action of ethoxycarbonylmethylenetriphenylphosphorane with the 5'-oxo-8,5'-cycloadenosine afforded the 5'-ethoxycarbonylmethylene-8,5'-cycloadenosine, which was converted to 5'-hydroxyethyl-5'-deoxy-8,5'-cycloadenosine by reduction with LiBH_4 followed by deacetonation. The 5'(R)- and 5'(S)-diastereomers of the 5'-hydroxyethyl derivative were separated and identified by NMR analysis. The circular dichroism (CD) spectra of the 5'-substituted-8,5'-cycloadenosines showed that the diastereomers having the substituent at the trans-gauche position around the C_4'-C_5' bond gave strong negative CD bonds, whereas the diastereomers with the 5'-substitutent at the gauche-trans position exhibited positive bands.

• 公益社団法人日本薬学会の論文
• 1980-03-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 松田 彰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  北海道大学薬学部

• 新妻 香穂里

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 新妻 香穂里

  Faculty Of Pharmaceutical Sciences Hokkaido University

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