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Site-selective modification of poly-ol derivatives utilizing organoboron catalyst

Research Project

Project/Area Number 18K14229
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

Kusano Shuhei  国立研究開発法人理化学研究所, 環境資源科学研究センター, 研究員 (80759291)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2018: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywordsベンゾオキサボロール触媒 / ポリオール / 位置選択的化学変換 / 分子認識 / グリコシル化 / 糖鎖 / 抗生物質 / 有機ホウ素触媒 / 糖類
Outline of Final Research Achievements

The site-selective modification of a polyol such a carbohydrate bearing multiple hydroxyl groups without protection groups is still challenging in synthetic organic chemistry. The sequential protection-deprotection steps on the hydroxyl groups require lengthy synthetic steps for accessing the functionalized-polyol compound, hence resulting in inefficient synthetic processes. To overcome this problematic issue in the poll modification, we in this study established a novel catalyst-controlled modification of polyols with the benzoxaborole catalyst. This methodology enables a straightforward synthesis of polyol derivatives including oligo saccharide and antibiotics

Academic Significance and Societal Importance of the Research Achievements

ポリオール類の直接的かつ位置選択的な化学変換法の開発は,糖鎖など創薬の中核を担う分子群の効率的合成を可能にするため合成化学分野の重要課題となっている.本研究で開発に成功したBO触媒によるポリオール類の化学変換反応は,直接性,位置選択性,誘導化されるポリオール類の構造多様性に優れる.したがって,本手法は,ポリオール類誘導体の効率的供給法として,ポリオール類に関連する創薬や生命科学研究の進展に大きく寄与すると期待される.

Report

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

    (5 results)

All 2020 2019 2018

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (1 results)

  • [Journal Article] Benzoxaborole Catalyst for Site-Selective Modification of Polyols2020

    • Author(s)
      Kusano Shuhei、Miyamoto Shoto、Matsuoka Aki、Yamada Yuji、Ishikawa Ryuta、Hayashida Osamu
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2020 Issue: 11 Pages: 1598-1602

    • DOI

      10.1002/ejoc.201901749

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Exciton-coupled circular dichroism-based glucose and galactose selective sensing in aqueous media with an anthracene-appended benzoxaborole dimer2020

    • Author(s)
      Kusano Shuhei、Ichikura Yuma、Fujimoto Kazuhiro J.、Konishi Sae、Yamada Yuji、Hayashida Osamu
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 7 Pages: 764-767

    • DOI

      10.1246/cl.200244

    • NAID

      130007872577

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Modular design for fluorophore homodimer probes using diethylentriamine as a common spacer2019

    • Author(s)
      Kusano Shuhei、Matsumoto Keisuke、Hayashida Osamu
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 17 Issue: 14 Pages: 3599-3603

    • DOI

      10.1039/c9ob00406h

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of water-soluble anthracene-appended benzoxaboroles and evaluation of their cis-1,2-diol recognition properties2018

    • Author(s)
      Kusano S.、Konishi S.、Yamada Y.、Hayashida O.
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 25 Pages: 4619-4622

    • DOI

      10.1039/c8ob00979a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Site-selective modification of polyol derivatives with organoboron catalyst2019

    • Author(s)
      草野 修平,萩原 伸也
    • Organizer
      日本化学会第99春季年会2019
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2021-02-19  

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