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Studies on Synthesis of Phospha-sugars by a New Route and Their Enzyme Inhibition

Research Project

Project/Area Number 10640521
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOKAYAMA UNIVERSITY

Principal Investigator

HANAYA Tadashi  Okayama Univ., Center of Instrumental Analysis, Assistant Professor, 機器分析センター, 助教授 (70189588)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO Hiroshi  Okayama Univ., Faculty of Science, Professor, 理学部, 教授 (70032828)
Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1998: ¥2,300,000 (Direct Cost: ¥2,300,000)
Keywordsphospha-sugar / C-P bond / D-galactofuranose / D-mannosamine / vicinal coupling constant / D-リボフラノース / D-グルコサミン / D-ガラクトース / ビジナル結合定数
Research Abstract

A New Route for Preparation of Pyranose-type Phospha-sugars.
D-gluco and L-idopyranose phospha-sugars were prepared in 6 steps, by starting with 3, 6-di-O-benzyl-1, 2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose.
2. Synthesis of D-Galactopyranose Phospha-sugar.
D-galactopyranose phospha-sugar was prepared in 6 steps, by starting with 3, 6-di-O-benzyl-1, 2-O-isopropylidene-β-L-arabino-hexofuranos-5-ulose.
3. Synthesis of D-mannosamine Phospha-sugar.
3, 6-Di-O-benzyl-5-O-deoxy-5-dimethylphosphinyl-1,2 O-isopropylidene-α-D-glucofuranose was converted, in 4 steps, into methyl 2-acetamido-3, 6-di-O-benzyl-2, 5-dimethoxyphosphinyl-α-D-mannofuranoside, which led to 3, 5-di-O-benzyl derivatives of D-mannosamine phospha-sugar.
4. The effect of a Phosphorus Atom upon Vicinal ィイD11ィエD1H-ィイD11ィエD1H Coupling Constants in Phospha-sugars.
Additivity constants for phosphorus were estimated for the prediction of vicinal ィイD11ィエD1H-ィイD11ィエD1H coupling constants by means of an additivity rule in a series of pyranose-type phospha-sugars.

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report

Research Products

(11 results)

All Other

All Publications (11 results)

  • [Publications] T. Hanaya: "The Effect of a Phosphorus Atom upon Vicinal ^1H-^1H Coupling Constants in Pyranose Derivatives Having a C-P Bond : Additivity Rule for the Effect of Phosphorus Substituents"Carbohydro. Res.. 306. 157-162 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Hanaya: "Synthesis of 2-Amino-2,5-dideoxy-5-hydroxyphosphinyl-D-Mannopyranose Derivative : New Phospho-sugar Analogues of D-Mannosamine"J. Chem. Res. (S). 790-791 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Hanaya: "A New Route for Preparation of 5-Deoxy-5-hydroxyphosphinyl-D-gluco-and L-idopyranose Derivatives"Heterocycles. 50. 323-332 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Hanaya and H. Yamamoto: "The Effect of a Phosphorus Atom upon Vicinal ィイD11ィエD1H-ィイD11ィエD1H Coupling Constants in Pyranose Derivatives Having a C-P Bond : Additivity Rule for the Effect of Phosphorus Substituents"Carbohydr. Res.. 306. 157-162 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Hanaya, Y. Fujii, and H. Yamamoto: "Synthesis of 2-Amino-2, 5-dideoxy-5-hydroxyphosphinyl-D-mannopyranose Derivatives : New Phospho-Sugar Analogs of D-Mannosamine"J. Chem. Res.. (S). 790-791 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T Hanaya, Y. Fujii, S. Ikejiri, and H. Yamamoto: "A New Route for Preparation of 5-Deoxy-5-hydroxyphosphinyl-D-gluco- and L-Idopyranose Derivatives"Heterocycles. 50. 323-332 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Hanaya: "A New Route for Preparation of 5-Deoxy-5-hydroxyphoshinyl-D-gluco-and L-idopyranose Derivatives"Heterocycles. 50. 323-332 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Hanaya: "Synthesis of 2-Amino-2,5-dideoxy-5-hydroxyphoshinyl-D-mannopyranose Derivatives : New Phospho-sugar Analogues of D-Mannosamine"J. Chem. Res. (S). 790-791 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Hanaya: "The Effect of a Phoshorus Atom upon Vicinal ^1Hー^1H Coupling Constants in Pyranose Derivatives Having a C-P Bond : Additivity Rule for the Effect of Phosphorus Substituents" Carbohydr.Res.306. 157-162 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hanaya: "A New Route for Preparation of 5-Deoxy-hydroxyphoshinyl-D-gluco-and L-idopyranose Derivatives" Heterocycles. 50. 323-332 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hanaya: "Synthesis of 2-Amino-2,5-dideoxy-5-hydroxyphosphinyl-D-mannopyranose Derivatives : New Phospho-suger Analogues of D-Mannosamine" J.Chem.Res.(S). 印刷中. (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-03-31   Modified: 2016-04-21  

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