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A synthetic methodology for selective substitution of inositol without protection and its use for preparation of useful functional materials

Research Project

Project/Area Number 23510257
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Living organism molecular science
Research InstitutionEhime University

Principal Investigator

WATANABE Yutaka  愛媛大学, 理工学研究科, 教授 (40114722)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsイノシトール / バイオマス / 選択的置換反応 / 光学活性 / 塩化リチウム / ジメチルアセトアミド / 酵素反応 / アルコールの活性化 / 置換反応 / 高分子 / LiCl / DMA / 無保護 / 有機合成 / 界面活性剤 / アシル化
Research Abstract

Myo-inositol is a promising material as a biomass. To realize this subject, a regioselective substitution on a desired OH group among six ones in inositol should be developed. It has been the most difficult problem, but we have found that dissolution of inositol in LiCl-dimethylacetamide or dimethylsulfoxide successfully promotes a substitution reaction to yield a regioselective 1,3-di-O- or 1-O-substitution product respectively depending on a amount of an electrophile. Desymmetrization of 1,3-diacetyl-myo-inositol by lipase produced monoacetate in a good yield with high optical purity (96% ee).
These fundamental research results directed us to design and synthesize a candidate of a surfactant and a monomer for a functional polymer, aiming at the use of myo-inositol as a biomass.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (22 results)

All 2014 2013 2012 2011 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (15 results) (of which Invited: 1 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Effects of 1,3-di-O-substituted-myo-inosiotl derivatives on the antiproliferation and caspase-3 activity of HCT-116 and HL-60 cells2014

    • Author(s)
      Noriyuki Hatae, Satoe Yamauchi, Takafumi Saeki, Ichiro Suzuki, Tominari Choshi, Satoshi Hibino, Chiaki Okada, Minoru Hayashi, Yutaka Watanbe, Eiko Toyota
    • Journal Title

      Chemical Biology Letters

      Volume: 1(2) Pages: 40-43

    • URL

      http://pubs.iscience.in/journal/index.php/cbl/article/view/135

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Specific Enhancement of Reactivity and Selectivity in the Substitution Reactions of Polyhydroxy Derivatives by Lithium Chloride2013

    • Author(s)
      Yutaka Watanabe, Mao Kawamoto, Hiroyuki Shintaku, Kae Tanabe, Hidetoshi Ohta, Minoru Hayashi
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 2(11) Issue: 11 Pages: 927-930

    • DOI

      10.1002/ajoc.201300163

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective functionalization of unprotected myo-inositol by electrophilic substitution2013

    • Author(s)
      Yutaka Watanabe, Tsuyoshi Uemura, Satoe Yamauchi, Kousei Tomita, Takafumi Saeki, Ryousuke Ishida, Minoru Hayashi
    • Journal Title

      Tetrahedron

      Volume: 69(23) Issue: 23 Pages: 4657-4664

    • DOI

      10.1016/j.tet.2013.03.109

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 酵素による非対称化を利用した光学活性イノシトール誘導体の合成2014

    • Author(s)
      北森 あゆみ・豊島 亮祐・太田 英俊・林 実・渡辺 裕
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Year and Date
      2014-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] 酵素による非対称化を利用した光学活性イノシトール誘導体の合成2014

    • Author(s)
      北森 あゆみ・豊島 亮祐・太田 英俊・林 実・渡辺 裕
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Related Report
      2013 Annual Research Report
  • [Presentation] LiCl と塩基によるジオールの立体配座識別に基づく選択的活性化による置換反応2013

    • Author(s)
      渡邉 裕・行定朋美・川本麻央・太田英俊・林 実
    • Organizer
      2013年日本化学会中国四国支部大会
    • Place of Presentation
      広島大学(東広島)
    • Year and Date
      2013-11-17
    • Related Report
      2013 Final Research Report
  • [Presentation] LiCl mediated acceleration and regioselection in the substitution reaction of polyols2013

    • Author(s)
      Yutaka Watanabe, Ryousuke Toyoshima, Kae Tanabe, Mao Kawamoto, Hiroyuki Shintaku, Hidetoshi Ohta, Minoru Hayashi
    • Organizer
      14th Tetrahedron Symposium
    • Place of Presentation
      Hilton Vienna (ウイーン、オーストリア)
    • Year and Date
      2013-06-27
    • Related Report
      2013 Final Research Report
  • [Presentation] LiCl mediated acceleration and regioselection in the substitution reaction of polyols2013

    • Author(s)
      Yutaka Watanabe, Ryousuke Toyoshima, Kae Tanabe, Mao Kawamoto, Hiroyuki Shintaku, Hidetoshi Ohta, Minoru Hayashi
    • Organizer
      14th Tetrahedron Symposium
    • Place of Presentation
      ウイーン(オーストリア)
    • Related Report
      2013 Annual Research Report
  • [Presentation] LiClと塩基によるジオールの立体配座識別に基づく選択的活性化による置換反応2013

    • Author(s)
      渡邉 裕・行定朋美・川本麻央・太田英俊・林 実
    • Organizer
      2013年日本化学会中国四国支部大会
    • Place of Presentation
      広島大学(東広島)
    • Related Report
      2013 Annual Research Report
  • [Presentation] myo-イノシトールの直接的修飾法の開発による 抗腫瘍活性化合物の探索2012

    • Author(s)
      波多江 典之,山内 智恵,久次米 永子,岡田知晃,岩村 樹憲, 渡邉 裕,豊田 栄子
    • Organizer
      第38回 反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2012-11-05
    • Related Report
      2013 Final Research Report
  • [Presentation] LiCl の制御によるポリオールの位置選択的置換反応2012

    • Author(s)
      渡辺 裕、石田良介、田邊佳恵、堀田佳佑、林実
    • Organizer
      第31回日本糖質学会年会
    • Place of Presentation
      鹿児島市民文化ホール(鹿児島)
    • Year and Date
      2012-09-18
    • Related Report
      2013 Final Research Report
  • [Presentation] LiClの制御によるポリオールの位置選択的置換反応2012

    • Author(s)
      渡辺裕、石田良介、田邊佳恵、堀田佳佑、林実
    • Organizer
      第31回日本糖質学会年会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Research-status Report
  • [Presentation] myo-イノシトールの直接的修飾法の開発による 抗腫瘍活性化合物の探索2012

    • Author(s)
      波多江 典之,山内 智恵,久次米 永子,岡田 知晃,岩村 樹憲, 渡邉 裕,豊田 栄子
    • Organizer
      第38回 反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] 直接置換基導入によるイノシトール誘導体の位置選択的合成2011

    • Author(s)
      石田良介、二宮雄樹、田邊佳恵、林 実、渡辺 裕
    • Organizer
      第27回若手化学者のための化学道場
    • Place of Presentation
      かんぽの宿伊野(いの町、高知)
    • Year and Date
      2011-09-09
    • Related Report
      2013 Final Research Report
  • [Presentation] 直接置換基導入によるイノシトール誘導体の位置選択的合成2011

    • Author(s)
      石田良介、二宮雄樹、田邊佳恵、林 実、渡辺 裕
    • Organizer
      第27回若手化学者のための化学道場
    • Place of Presentation
      高知
    • Related Report
      2011 Research-status Report
  • [Presentation] myo-イノシトールへの位置選択的置換基導入と酵素を用いた光学分割

    • Author(s)
      北森 あゆみ、豊島 亮祐、太田 英俊、林 実、渡辺 裕
    • Organizer
      2013ハロゲン利用ミニシンポジウム
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Annual Research Report
  • [Presentation] LiClによるポリオールの活性化による 選択的置換反応

    • Author(s)
      行定朋美・川本麻央・新宅弘幸・太田英俊・林 実・渡辺 裕
    • Organizer
      2013ハロゲン利用ミニシンポジウム
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Annual Research Report
  • [Presentation] LiCl mediated acceleration and regioselection in the substitution reaction of polyols

    • Author(s)
      Yutaka Watanabe
    • Organizer
      mini-Symposium
    • Place of Presentation
      ミュンヘン工科大学(ドイツ)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Book] A Straightforward Synthesis and Biological Activity of 1,3-Di-O -substituted myo-Inositol Derivatives, "Rice Studies, Present and Future"2012

    • Author(s)
      Noriyuki Hatae, Satoe Yamauchi, Minoru Ishikura, Tatsunori Iwamuraa and Yutaka Watanabe
    • Publisher
      三共出版株式会社、Seiichiro Ogawa (編集)
    • Related Report
      2013 Final Research Report
  • [Book] Rice Studies, Present and Future2012

    • Author(s)
      Seiichiro Ogawa (Editor)
    • Total Pages
      341
    • Publisher
      三共出版株式会社
    • Related Report
      2012 Research-status Report
  • [Remarks] 愛媛大学大学工学部応用化学科反応有機化学

    • URL

      http://www.ehime-u.ac.jp/~achem/orgrea/index.html

    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://kenqweb.office.ehime-u.ac.jp/yoran/

    • Related Report
      2011 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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