Chemistly of O-Silylated Ketene Acetals : Stereocontrolled Synthesis of 3-Benzoylamino-2,3-dideoxy-pentoses by a 1,3-Addition to Chiral Nitrones

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概要

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• The stereochemistry of 1,3-addition of ketene acetals (1a, b) to the chiral nitrones (4a-d) derived from 2,3-O-isopropylidene-D-glyceraldehyde was examined. The reaction of ketene methyl tert-butyldimethylsilyl acetal (1a) with the N-benzylnitrone (4a) produced a syn-1,3-adduct (5a) predominantly, while the reaction of ketene tert-butyl tert-butyldimethylsilyl acetal (1b) with the N-diphenylmethylnitrone (4d) gave an anti-1,3-adduct (5h) predominantly. These adducts were readily transformed into the corresponding 3-benzoylamino-2,3-dideoxypentoses (10a, b).

• 社団法人日本薬学会の論文
• 1989-08-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• 北 泰行

  Faculty of Pharmaceutical Sciences, Osaka University

• 北 泰行

  大阪大学大学院薬学研究科

• Kita Yasuyuki

  Graduate School Of Pharmaceutical Sciences Osaka University Yamadaoka

• 田村 修

  Faculty of Pharmaceutical Sciences, Osaka University

• 三木 隆

  Faculty Of Pharmaceutical Sciences Osaka University

• 伊藤 文雄

  Pharmaceutical Research Laboratories Iii Takeda Chemical Industries Ltd.

• 伊藤 文雄

  Faculty of Pharmaceutical Sciences, Osaka University

• 岸野 浩子

  Faculty of Pharmaceutical Sciences, Osaka University

• 河野 昌子

  Faculty of Pharmaceutical Sciences, Osaka University

• 田村 修

  Faculty Of Pharmaceutical Sciences Osaka University

• 田村 修

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 河野 昌子

  Faculty Of Pharmaceutical Sciences Osaka University

• 北 泰行

  Faculty Of Pharmaceutical Sciences Osaka University

• 岸野 浩子

  Faculty Of Pharmaceutical Sciences Osaka University

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