Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose

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概要

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• In order to obtain a 3-C-hydroxymethyl-D-glucose derivative some nucleophilic reactions of 1,2 : 5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (1) and the configurations of products have been examined. Gluco-and allo-configurations of known 3-C-nitromethyl derivatives of 1 were confirmed by the fact that 3-C-acetaminomethyl-1,2-O-isopropylidene-α-D-xylo- and ribo-pentodialdofuranoses, derived by four successive transformations, showed the absence and presence of the aminal-ring formation between the aldehyde and acetamino groups, respectively. A 3-C-carbethoxymethyl derivative obtained by the Reformatsky reaction of 1 with ethyl bromoacetate was proved to be of allo-configuration by the lactone-formation between C5-hydroxyl and carboxyl groups. The configuration of 3-C-hydroxymethyl derivative (15) obtained by treatment of known 3-C-methylene derivative of 1 with permanganate was proved to be of gluco-typc by comparison of the corresponding 3-C-aminomethyl derivative (5), derived by three-step conversions, with that obtained from 3-C-nitromethyl derivatives. 15 was also obtained by epoxidation of 1 with diazomethane followed by ring-opening with alkali. Treatment of 5 and its allo-epimer with nitrous acid gave, respectively, a ring-expanded product and the 3′,5-anhydride, the former being also recognized in the epoxidation products. Structures of new compounds were examined by NMR spectra and stereoselectivity of reactions discussed.

• 日本化学会の論文

著者

• 佐藤 憲一

  Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University

• Funabashi Masuo

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• 吉村 寿次

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Yoshimura Juji

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Kobayashi Kazuhiko

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

関連論文

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• Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose
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