Thio-Sugars. I. Radical-Promoted Thione-Thiol Rearrangement of Cyclic Thionocarbonates : Synthesis of 5-Thioglucose

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概要

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• The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2,when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other, hand, theromolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.

• 公益社団法人日本薬学会の論文
• 1996-08-15

著者

• 佐藤 美洋

  北海道大学大学院薬学研究院

• Sato Y

  Osaka Prefecture University

• Sato Y

  (present Address)tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Nakao Keiko

  Kyoto Pharmaceutical University

• Ishikawa Y

  Sumitomo Metal Ind. Kyoto Jpn

• TSUDA YOSHISUKE

  Faculty of Pharmaceutical Sciences, Kanazawa University

• HOSOI Shinzo

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 佐藤 嘉信

  Department Of Chemical Engineering University Of Osaka Prefecture

• Nakao Kayo

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Hosoi S

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Hosoi Shinzo

  Faculty Of Pharmaceutical Sciences Kanazawa University

• KANEMITSU Kimihiro

  (Present address)Ishikawa-ken Red Cross Blood Centre

• SATO Yoshiyuki

  (Present address)Tsukuba Research Institute, Banyu Pharmaceutical Co., Ltd.,

• Tsuda Yoshisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• SHIBAYAMA Kenji

  Faculty of Pharmaceutical Sciences, Kanazawa University

• ISHIKAWA Yuko

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Kanemitsu K

  (present Address)ishikawa-ken Red Cross Blood Centre

• Shibayama K

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Shibayama Kenji

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Ishikawa Yuko

  Faculty Of Education Fukushima University

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