Stereocontrolled general synthesis of pyrimidine C-nucleosides having branched-chain sugar moieties.
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概要
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A variety of pyrimidine <I>C</I>-nucleosides bearing branched-chain sugars can be synthesized starting from adequately substituted (1<I>R</I><SUP>*</SUP>,6<I>S</I><SUP>*</SUP>,7<I>S</I><SUP>*</SUP>,8<I>R</I><SUP>*</SUP>)-7,8-isopropylidenedioxy-3,9-dioxabicyclo[4.2.1]nonan-4-ones. The general procedure consists of condensation with <I>t</I>-butoxybis(dimethylamino) methane, giving the corresponding α-dimethylaminomethylene lactones, base-catalyzed heterocycle formation with urea, thiourea, or guanidine, and acid-promoted removal of the isopropylidene protective group. The overall transformation proceeds with retention of the stereochemistry to afford only <I>C</I>-β-glycosyl nucleoside structures.
- 公益社団法人 日本化学会の論文
著者
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Noyori Ryoji
Department Of Chemistry And Molecular Chirality Research Unit Nagoya University
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Sato Tsuneo
Department Of Life Science Kurashiki University Of Science And The Arts
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Kobayashi Hiroshi
Department Of Applied Physics School Of Science And Engineering Waseda University
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Watanabe Makoto
Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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Watanabe Makoto
Department of Chemistry, Nagoya University
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Sato Tsuneo
Department of Chemistry, Nagoya University
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