Stereospecific and stereoselective reactions. IX. Preparation of ethyl (2E,7R)-7-acetoxy-4-oxo-2-octenoate from D-glucose.
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概要
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Reaction of methyl 2,3-anhydro-4,6-dideoxy-α-D-<I>ribo</I>-hexopyranoside with MgI<SUB>2</SUB> exclusively afforded methyl 3,4,6-trideoxy-3-iodo-α-D-<I>xylo</I>-hexopyranoside which was dehalogenated by treatment with LiAlH<SUB>4</SUB> to give methyl 3,4,6-trideoxy-α-D-<I>erythro</I>-hexopyranoside (<B>2</B>). Hydrolysis of <B>2</B> and subsequent treatment with ethoxycarbonylmethylenetriphenylphosphorane gave ethyl (2<I>E</I>, 4<I>R</I>, 7<I>R</I>)-4,7-dihydroxy-2-octenoate (<B>10</B>). Oxidation of <B>10</B> by-active MnO<SUB>2</SUB> resulted in the formation of an equilibrium mixture of ethyl (2<I>E</I>, 7<I>R</I>)-7-hydroxy-4-oxo-2-octenoate (the carbon skeleton of pyrenophorin) and cyclic hemiacetal. On treatment with acetic anhydride, the mixture afforde dethyl (2<I>E</I>, 7<I>R</I>)-7-acetoxy-4-oxo-2-octenoate.
- 公益社団法人 日本化学会の論文
著者
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Mitsunobu Oyo
Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University
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Yokota Sumio
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University
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Nishida Mitsuru
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University
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