Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring : Formation of cis-Arranged Cyclic Thiolcarbonates

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概要

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• Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in accepTable yields.2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides(peracetate forms) by conventional means.

• 公益社団法人日本薬学会の論文
• 1997-06-15

著者

• 佐藤 美洋

  北海道大学大学院薬学研究院

• 関川 善夫

  Department Of Pharmaceutical Sciences National Institute Of Public Health

• Sato Y

  Osaka Prefecture University

• Sato Y

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

• Sato Y

  Kyoritsu College Of Pharmacy

• 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

• Hosoi S

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Hosoi Shinzo

  Faculty Of Pharmaceutical Sciences Kanazawa University

• NOGUCHI Shinsuke

  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.,

• KAKIMOTO Kyoko

  Faculty of Pharmaceutical Sciences, Kanazawa University

• IWAKURA Yumiko

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Iwakura Yumiko

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Kakimoto Kyoko

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Tsuda Yoshisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Kanemitsu K

  (present Address)ishikawa-ken Red Cross Blood Centre

• Tsuda Y

  Faculty Of Pharmaceutical Sciences And High Technology Research Center Kobe Gakuin University

• Noguchi Shinsuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

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