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Development of solid catalysts for direct synthesis of unsaturated sugar derivatives from sugars without protecting groups

Research Project

Project/Area Number 18K18965
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 27:Chemical engineering and related fields
Research InstitutionTohoku University

Principal Investigator

Tamura Masazumi  東北大学, 工学研究科, 助教 (10635551)

Project Period (FY) 2018-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2019: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2018: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Keywords脱酸素脱水反応 / メチルグリコシド / 不均一系触媒 / ジデオキシ糖 / 脱酸素脱水 / ポリオール / キラル化合物 / 水素化 / 触媒・化学プロセス
Outline of Final Research Achievements

Transformation of sugar derivatives generally requires protecting and deprotecting of the OH groups, which causes multi-step reactions, low yields and formation of a large amount of wastes. Therefore, development of effective catalysts, particularly heterogeneous catalysts in terms of the recoverability and reusability, which can selectively transform the sugar derivatives without protecting of OH groups is highly desirable. In this study, we found that ReOx-dpAu/CeO2, which was prepared by the deposition-precipitation method, was an effective and reusable heterogeneous catalyst for the direct deoxydehydration (DODH) reaction of methyl glycosides to provide the corresponding dideoxy unsaturated methyl glycosides in high yields without protecting the OH groups.

Academic Significance and Societal Importance of the Research Achievements

糖類はバイオマス由来の基幹化合物であり、糖類を直接かつ高選択的に有用化学品に変換する技術の開発が強く望まれている。本研究により開発された技術は、糖類の水酸基を保護することなく、直接かつ一段で有用化合物であるジデオキシ不飽和糖を生成できるものであり、これまでの、多段階合成に比べ、廃棄物、エネルギー、コストを削減できる手法と考えられ、また、生成したジデオキシ糖を加水分解、水素化することで、キラルポリオールに変換したり、不飽和結合を官能基変換したりすることが可能であると考えらえる。今後、更なる触媒性能の向上、基質の適用範囲の拡大により、実用化が強く期待される。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (8 results)

All 2019 2018

All Journal Article (2 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 2 results) Presentation (6 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results)

  • [Journal Article] Synthesis of Hexane-Tetrols and -Triols with Fixed Hydroxyl Group Positions and Stereochemistry from Methyl Glycosides over Supported Metal Catalysts2019

    • Author(s)
      Krishna Siddarth H.、Cao Ji、Tamura Masazumi、Nakagawa Yoshinao、De Bruyn Mario、Jacobson Graeme S.、Weckhuysen Bert M.、Dumesic James A.、Tomishige Keiichi、Huber George W.
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 8 Issue: 2 Pages: 800-805

    • DOI

      10.1021/acssuschemeng.9b04634

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Direct Synthesis of Unsaturated Sugars from Methyl Glycosides2019

    • Author(s)
      Cao Ji、Tamura Masazumi、Nakagawa Yoshinao、Tomishige Keiichi
    • Journal Title

      ACS Catalysis

      Volume: 9 Issue: 4 Pages: 3725-3729

    • DOI

      10.1021/acscatal.9b00589

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Direct Synthesis of Dideoxy Sugars from Methyl Glycosides by Using Heterogeneous Catalysts2019

    • Author(s)
      Masazumi Tamura
    • Organizer
      The 1st International Symposium on Hybrid Catalysis for Enabling Molecular Synthesis on Demand
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 糖類からの選択的かつ直接的ジデオキシ糖類合成用触媒の開発2019

    • Author(s)
      田村正純、Ji Cao、中川善直、冨重圭一
    • Organizer
      第115回有機合成シンポジウム2019年【春】
    • Related Report
      2019 Annual Research Report
  • [Presentation] 糖類からの選択的かつ直接的ジデオキシ糖類合成用触媒の開発2019

    • Author(s)
      田村正純、CaO Ji、中川善直、冨重圭一
    • Organizer
      第115回有機合成シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] Selective Transformation of Methyl Glycosides to Useful Chemicals over Heterogeneous Catalysts2018

    • Author(s)
      Masazumi TAMURA
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Selective hydrodeoxygenation of methyl glycosides to dideoxy products by heterogeneous ReOxPd/CeO2 catalyst2018

    • Author(s)
      CAO, Ji・TAMURA, Masazumi・NAKAGAWA, Yoshinao・TOMISHIGE, Keiichi
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Hydrodeoxygenation of vicinal OH groups in methyl glycosides over palladium modified CeO2 supported rhenium catalyst2018

    • Author(s)
      Ji CAO, Naoto YUASA, Masazumi TAMURA, Yoshinao NAKAGAWA, Keiichi TOMISHIGE
    • Organizer
      The 8th Tokyo Conference on Advanced Catalytic Science and Technology (TOCAT8)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research

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Published: 2018-07-25   Modified: 2021-02-19  

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