Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates : Formation of Branched Furanosides
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概要
- 論文の詳細を見る
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
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津田 喜典
金沢大学
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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西村 誠
(present Address)fuji Chemical Industry Ltd.
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伊藤 洋子
Faculty of Pharmaceutical Sciences, Kanazawa University
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伊藤 洋子
Faculty Of Pharmaceutical Sciences Kanazawa University
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