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The ring-opening and ring-forming polymerization of diepoxides and diepisulfides leading to novel carbohydrate

Research Project

Project/Area Number 10450348
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionHOKKAIDO UNIVERSITY

Principal Investigator

KAKUCHI Toyoji kazuaki  Hokkaido Univ., Grad.School of Envirn.Earth Sci., Asso.Prof., 大学院・地球環境科学研究科, 助教授 (80113538)

Co-Investigator(Kenkyū-buntansha) KAGA Harumi  Hokkaido National Industrial Research Institute, Senior Researcher, 北海道工業技術研究所・機能物質化学研究室, 室長(研究職)
SATHO Toshifumi  Hokkaido Univ., Grad.School of Eng., Lect., 大学院・工学研究科, 助手 (80291235)
YOKOTA Kazuaki  Hokkaido Univ., Grad.School of Eng., Prof., 大学院・工学研究科, 教授 (30001217)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥11,200,000 (Direct Cost: ¥11,200,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1999: ¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 1998: ¥5,300,000 (Direct Cost: ¥5,300,000)
KeywordsCyclopolymerization / Diahynydro pentitol / Diahnydro hexitol / Diastereoselective cyclopolymerization / L-Arabinitol / Xilitol / Allitol / Galactitol / ジエピスルフィド / 環化重合 / 光学活性高分子 / 5員環構造 / 非環化構造 / イオノフォア / D-マンニトール / D-アラビニトール / 液膜 / 光学分割 / アドニトール / キシリトールユニット / ガラクチドル / アラビニトール / 新規糖鎖
Research Abstract

The research aimed to establish the synthesis of novel polymers consisting of heterocyclic units by the ring-opening and ring-forming polymerization of bifunctional monomers, such as 1)the cyclopolymerization of chiral dianhyro pentitol, 2)the cyclopolymerization of meso diahnydro pentitol and meso diahnydro hexitol, and 3)the diastereoselective cyclopolymerization of meso diepisulfide.
1)The cationic polymerization of the chiral dianhyro pentitol, 1, 2 : 4, 5-dianhydro-3-O-methyl-L-arabinitol was regeo-and stereoselective to form the organic solvent-soluble polymer consisting 1, 4-anydro-3-O-methyl-adonitol units.
2)For meso-diepoxides, the cationic polymerization of 1, 2 : 4, 5-dianhydro-3-O-methyl-xilitol proceeded as well as the chiral dianhyro pentitol to produce the carbohydrate polymer consisting 1, 4-anydro-3-O-methyl-arabinitol units. In addition, the cyclopolymerization of a meso hexitol, 1, 2 : 5, 6-dianhydro-3, 4-di-O-methyl-allitol, produced the polymers consisting of the 5-and 6-membered cyclic units using anionic and cationic initiators, respoctively. For 1, 2 : 5, 6-dianhydro-3, 4-di O-methyl-galactitol, the polymerization using the anionic initiator was regeo-and stereoselective, whereas the cationic one was not regular.
3)The polymerization of a meso-diepisulfide, which was synthesized from 1, 2 : 5, 6-dianhydro-3, 4-di-O-methyl-galactitol, using the chiral zinc complex was diastereoselective to afford the chiral polymer consisting of the 5-membered cyclic and uncyclic units.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (41 results)

All Other

All Publications (41 results)

  • [Publications] T.Hatakeyama: ""Living" nature in anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol using potassium tert-butoxide/18-crown-6 initiating system"Macromolecules. 31. 2889-2893 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Umeda: "Synthesis of (1→6)-2,5-anhydro-D-glucitol through cyclopolymerization of 3,4-di-O-allyl-1,2:5,6-dianhydro-D-mannitol and optical resolution ability of its derivative in HPLC"Journal of Polymer Science, Part A-Chemistry Edition. 36. 901-909 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh: "Enatioselective permeability of the membranes prepared from polyacrylonitrile-graft-(1→6)-2,5-anhydro-D-glucitol"Reactive and Functional Polymers. 37. 293-298 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kamada: "Asymmetric Cyclization of meso-Diepoxides using Chiral (salen) Co (III) OAc Catalyst Forming Optically Active 1,4-Anhydropentitols and 2,5-Anhydrohexitols"Tetrahadron Asymmetry. 10. 3667-3670 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kamada: "Regio-and stereoselective cyclopolymerization of 1,2:5,6-dianhydro-allitol and 1,2:5,6-dianhydro-galactitol leading to a novel carbohydrate polymer of (2→6)-1,5-anhydro-DL-galactitol"Macromolecules. 32. 5755-5759 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi: "Macromolecular ionophore. 2. Metal cation-binding property of (1→6)-2,5-anhydro-D-glucitol"Polymer Journal. 31. 293-295 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh: "Regio-and Stereoselective Cyclopolymerization of 1,2:4,5-Dianhydro-3-O-methyl-xylitol Leading to A Novel Polycarbohydrate of (2→5)-1,4-Anhydro-3-O-methyl-pentitol"Macromolecular Rapid Communication. 20. 55-58 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh: "Cyclopolymerization of 1,2:5,6-Diepithio-3,4-di-O-methyl-1,2,5,6-tetradeoxy-D-mannitol and-L-iditol Leading to a Novel Thio-Sugar"Macromolecules. 33. 5303-5307 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Yokota: "Synthesis of A Noel Polymeric Carbohydrate via Regio-and Stereoselective Cyclopolymerization of 1,2:5,6-Dianhydrohexitol"Macromolecular Symposia. 157. 13-20 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi: "Cationic ring-opening polymeriztion of 1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose as a convenient synthesis of dextran"Macromol. Rapid Comun.. 21. 1003-1006 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Umeda: "A novel chiral stational phase in HPLC. Optical resolution of racemic amino compounds by (1→6)-2,5-anhydro-3,4-di-O-ethyl-D-glucitol bound on silica gel"Enantiomer. 5. 473-479 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 覚知豊次: "液膜による光学分割"膜. 25. 273-276 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi: "Ring-opening and ring-forming polymerization of 1,2:5,6:9,10-triepoxydecane leading to highly regioselective polymer consisting of octahydrobifuranyl unit"Macromolecules. 33. 246-247 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Yokota: "Syntheses of novel carbohydrate polymers via regio-and stereoselective cyclopolymerization of 1,2:5,6-dianhydrohexitols"Recent Research Developments in Polymer Science. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hatakeyama, M.Kamada, T.Satoh, K.Yokota and T.Kakuchi: ""Living" nature in anionic cyclopolymerization of 1, 2 : 5, 6-dianhydro-3, 4-di-O-methyl-D-mannitol using potassium tertbutoxide/18-crown-6 initiating system"Macromolecules. 31. 2889-2893 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Umeda, T.Satoh, T.Hatakeyama, K.Yokota and T.Kakuchi: "Synthesis of(1→6)-2, 5-anhydro-D-glucitol through cyclopolymerization of 3, 4-di-O-allyl-1, 2 : 5, 6-dianhydro-D-mannitol and optical resolution ability of its derivative in HPLC"Journal of Polymer Science, Part A-Chemistry Edition. 36. 901-909 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh, Y.Tanaka, K.Yokota and T.Kakuchi: "Enatioselective permeability of the membranes prepared from polyacrylonitrile-graft-(1→6)-2, 5-anhydro-D-glucitol"Reactive and Functional Polymers. 37. 293-298 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kamada, T.Satoha, T.Kakuchib and K.Yokota: "Asymmetric Cyclization of meso-Diepoxides using Chiral(salen)Co(III)OAc Catalyst Forming Optically Active 1, 4-Anhydropentitols and 2, 5-Anhydrohexitols"Tetradron Asymmetry. 10. 3667-3670 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kamada, T.Satoh, K.Yokota and T.Kakuchi: "Regio-and Stereoselective Cyclopolymerization of 1, 2 : 5, 6-Dianhydro-allitol and 1, 2 : 5, 6-Dianhydro-galactitol Leading to A Novel Carbohydrate Polymer of(2→6)-1, 5-anhydro-DL-galactitol"Macromolecules. 32. 5755-5759 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi, T.Hatakeyama, Kanai, T.Satoh, K.Yokota, H.Kaga and K.Haraguchi: "Macromolecular ionophore. 2. Metal cation-binding property of(1→6)-2, 5-anhydro-D-glucitol"Polymer Journal. 31. 293-295 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh, K.Shibata, K.Yokota and T.Kakuchi: "Regio-and Stereoselective Cyclopolymerization of 1, 2 : 4, 5-Dianhydro-3-O-methyl-xylitol Leading to A Novel Polycarbohydrate of(2→5)-1, 4-Anhydro-3-O-methyl-pentitol"Macromolecular Rapid Communication. 20. 55-58 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Satoh, D.Kitazawa, R.Nonokawa, M.Kamada, K.Yokota, H.Hashimoto and T.Kakuchi: "Cyclopolymerization of 1, 2 : 5, 6-Diepithio-3, 4-di O-methyl-1, 2, 5, 6-tetradeoxy-D-mannitol and-L-iditol Leading to a Novel Thio-Sugar"Macromolecules. 33. 5303-5307 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Yokota, T.Kakuchi, T.Satoh, S.Umeda and M.Kamada: "Synthesis of A Noel Polymeric Carbohydrate via Regio-and Stereoselective Cyclopolymerization of 1, 2 : 5, 6-Dianhydrohexitol"Macromolecular Symposia. 157. 13-20 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi, A.Kusuno, M.Miura and H.Kaga: "Cationic ring-opening polymeriztion of 1, 6-anhydro-2, 3, 4-tri-O-allyl-β-D-glucopyranose as a convenient synthesis of dextran"Macromolecular Rapid Comunication. 21. 1003-1006 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Umeda, T.Satoh, K.Saitoh, H.Kanai, M.Kamada, K.Yokota and T.Kakuchi: "A novel chiral stational phase in HPLC.Optical resolution of racemic amino compounds by(1→6)-2, 5-anhydro-3, 4-di-O-ethyl-D-glucitol bound on silica gel"Enantiomer. 5. 473-479 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi, S.Umeda, T.Satoh and K.Yokota: "Optical resolution using liquid membrane"Membrane(Japanese). 25. 273-276 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi, R.Nonokawa, S.Umeda, T.Satoh and K.Yokota: "Ring-opening and ring-forming polymerization of 1, 2 : 5, 6 : 9, 10-triepoxydecane leading to highly regioselective polymer consisting of octahydrobifuranyl unit"Macromolecules. 33. 246-247 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Yokota, H.Hashimoto, T.Satoh, S.Umeda and T.Kakuchi: "Syntheses of novel carbohydrate polymers via regio-and stereoselective cyclopolymerization of 1, 2 : 5, 6-dianhydrohexitols"Recent Research Developments in Polymer Science. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kakuchi: "Ring-opening and ring-forming polymerization of 1,2 : 5,6 : 9,10-triepoxydecane leading to highly regioselective polymer consisting of octahydrobifuranyl unit"Macromolecules. 33. 246-247 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh: "Cyclopolymerization of 1,2 : 5,6-Diepithio-3,4-di-O-methyl-1,2,5,6-tetradeoxy-D-mannitol and -L-iditol Leading to a Novel Thio-Sugar"Macromolecules. 33. 5303-5307 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Yokota: "Synthesis of A Noel Polymeric Carbohydrate via Regio- and Stereoselective Cyclopolymerization of 1,2 : 5,6-Dianhydrohexitol"Macromolecular Symposia. 157. 13-20 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Kakuchi: "Cationic ring-opening polymeriztion of 1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose as a convenient synthesis of dextran"Macromol.Rapid Comun.. 21. 1003-1006 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Umeda: "A novel chiral stational phase in HPLC. Optical resolution of racemic amino compounds by (1→6) -2,5-anhydro-3,4-di-O-ethyl-D-glucitol bound on silica gel"Enantiomer. 5. 473-479 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 覚知豊次: "液膜による光学分割"膜. 25. 273-276 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T. Kakuchi: "Ring-opening and Ring-forming Polymerization of 1,2:5,6:9,10-Triepoxydecane Leading to Highly Regioselective Polymer Consisting of Octahydrobifuranyl Unit"Macromolecules. 33. 246-247 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] M. Kamada: "Regio- and Stereoselective Cyclopolymerization of 1,2:5,6-Dianhydro-allitol and 1,2:5,6-Dianhydro-galactitol Leading to A Novel Carbohydrate Polymer of (2→6)-1,5-anhydro-DL-galactitol"Macromolecules. 32. 5755-5759 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Satoh: "Regio- and Stereoselective Cyclopolymerization of 1,2:4,5-Dianhydro-3-0-methyl-xylitol Leading to A Novel Polycarbohydrate of (2→5)-1,4-Anhydro-3-0-methyl-pentitol"Macromolecular Rapid Communication. 20. 55-58 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Satoh: "Regio- and Stereoselective Cyclopolymerization of 1,2:4,5-Dianhydro-3-O-methyl-xylitol Leading to A Novel Polycarbohydrate of(2→5)-1,4-Anhydro-3-O-methyl-pentitol" Macromolecular Rapid Communication. 20. 55-58 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hatakeyama: "“Living" nature in anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol using potassium tert-butoxide/18-crown-6 initiating system" Macromolecules. 2889-2893 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Satoh: "Enatioselective permeability of the membranes prepared from polyacrylonitrile-graft-(1→6)-2,5-anhydro-D-glucitol" Reactive and Functional Polymers. 37. 293-298 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Umeda: "Synthesis of(1→6)-2,5-anhydro-D-glucitol through cyclopolymerization of 3,4-di-O-allyl-1,2:5,6-dianhydro-D-mannitol and optical resolution ability of its derivative in HPLC" Journal of Polymer Science,Part A-Chemistry Edition. 36. 901-909 (1998)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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