Aminosugars. XXVIII. A Facile Synthesis of Benzyl α- and β-Kasugaminides via the Corresponding Abequosides

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概要

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• Synthesis of benzyl α- and β-kasugaminides (benzyl 2,4-diamino-2,3,4,6-tetradeoxy-α- and β-D-arabino-hexopyranosides) was carried out by the simultaneous substitution at 2,4-positions of 2,4-di-O-mesyl-abequosides (3,6-dideoxy-2,4-di-O-mesyl-α- and β-D-xylo-hexopyranosides) with sodium azide followed by hydrogenation. The substitution in N,N-dimethylformamide at higher temperature gave the elimination products (4-azido-2,3-unsaturated derivatives) and the subsequently rearranged products (3,4-unsaturated 2-azido derivatives), but, that in hexamethylphosphoric triamide at lower temperature gave the desired compounds in fairly good yields.

• 日本化学会の論文

著者

• SATO Ken-ichi

  Laboratory of Molecular Biology, Biosignal Research Center, Kobe University

• 佐藤 憲一

  Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University

• 吉村 寿次

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

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Hashimoto Hironobu

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

• Shimizu Kuniaki

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

• Sato Ken-ichi

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

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