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The Development of new Methods for the Deoxygenation of Sugars

Research Project

Project/Area Number 62840015
Research Category

Grant-in-Aid for Developmental Scientific Research

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionGunma University

Principal Investigator

MIGITA Toshihiko  Faculty of Engineering, Gunma University, 工学部, 教授 (40008412)

Co-Investigator(Kenkyū-buntansha) SANO Hiroshi  Faculty of Engineering, Gunma University, 工学部, 助手 (40162523)
Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1988: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1987: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsdeoxygenation / acetylated sugar / deoxysugar / トリフェニルシラン
Research Abstract

Deoxygenation of sugars occupies a significant position in carbohydrate chemistry. Although there have been numerous methods for the deoxygenation via various intermediates, reports of satisfactory methods for the deoxygenation of acetylated sugars, which were often utilized in sugar chemistry, are rare. We have then investigated new efficient routes for the transformation of sugar compounds to deoxysugars.
1. Triphenylsilane is a good deoxygenating reagent for the transformation of acetylated sugars to deoxysugars. The deoxygenation has a advantage that the acetylated sugars can be deoxygenated without affecting the other functinalities such as acetals, since the reaction proceeds under neutral conditions.
2. p-bis(diphenylhydrosilyl)benzene is a excellent reducing reagent for the deoxygenation of acetylated sugars, since the deoxygenation proceeds completely with less amount of the reducing agent compared with the case of triphenylsilane. Furthermore, the resulting deoxysugars can be easily isolated from the reaction mixture, since the by-products derived from the reagent are high boiling compounds.

Report

(2 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] H.Sano: Chem.Lett.77-80 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H.Sano: Chem.Lett.119-122 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H.Sano: Synthesis. 402-403 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H. Sano: "Reductive Deoxygenation of Alcohols via Esters with Triphenylsilane under Neutral Conditions" Chem. Lett.,. 77-80 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H. Sano: "p-Bis(diphenylhydrosilyl)benzene. A Useful Reagent for the Doxygenation of Alcohols Via Acetates" Chem. Lett.,. 119-122 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H. Sano: "A Novel Method for the Deoxygenation of Acetylated Sugars" Synthesis. 402-403 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H.Sano: Chem.Lett.77-80 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Sano: Chem.Lett.119-122 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Sano: Synthesis. 402-403 (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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