Synthesis of 2'-Deoxy-6,2'-methano-cyclouridine (Nucleosides and Nucleotides. LIX)
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概要
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2'-Deoxy-6,2'-methano-cyclouridine, a carbon-bridged cyclonucleoside fixed in a high-anti conformation, was synthesized. Treatment of a 3', 5'-O-protected 6-cyano-2'-O-imidazolythiocarbonyluridine with tri-n-butyltin hydride afforded a 6,2'-oxomethano-cyclouridine derivative in low yield. Base treatment of 5-bromo-2'-deoxy-2' (S)-ethoxycarbonylmethyl-3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl) uridine resulted in an intramolecular Michael reaction followed by dehydrobromination to give the 6,2'-cyclonucleoside. The latter was de-ethoxycarbonylated by treatment with sodium chloride and water in dimethylsulfoxide followed by desilylation to furnish the title compound.
- 社団法人日本薬学会の論文
- 1985-09-25
著者
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上田 亨
Faculty of Pharmaceutical Science, Hokkaido University
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上田 亨
Faculty Of Pharmaceutical Sciences Hokkaido University
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佐野 友春
Faculty of Pharmaceutical Sciences, Hokkaido University
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井上 英夫
Faculty of Pharmaceutical Sciences, Hokkaido University
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井上 英夫
北海道大学薬学部
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佐野 友春
Faculty Of Pharmaceutical Sciences Hokkaido University
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上田 亨
北海道大学薬学部
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井上 英夫
Faculty Of Pharmaceutical Sciences Hokkaido University
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