Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates : Formation of Branched Furanosides

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概要

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• Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions : (1) stereospecific 1,2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O : for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.

• 公益社団法人日本薬学会の論文
• 1991-08-25

著者

• 津田 喜典

  金沢大学

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 西村 誠

  (present Address)fuji Chemical Industry Ltd.

• 伊藤 洋子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 伊藤 洋子

  Faculty Of Pharmaceutical Sciences Kanazawa University

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