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Synthesis of Sphingosines and Cerebrosides

Research Project

Project/Area Number 61570993
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

NAKAGAWA Masako  Faculty of Pharmaceutical Sciences, Chiba University, 薬学部, 助教授 (40009171)

Co-Investigator(Kenkyū-buntansha) HINO Tohru  Faculty of Pharmaceutical Sciences, Chiba University, 薬学部, 教授 (10009160)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsスフインゴシン / セラミド / セレブロサイド / セレブロサイドBb / ニトロエタノール / アルドール反応 / α-ハイドロキシパルミチン酸 / (±)-スフインゴシン / ニトロアルコール
Research Abstract

1. Synthesis of racemic sphingosine 1, the corresponding ceramide 2, and cerebroside 3 and related compounds were accomplished by newly developed our method for synthesis of aminodiols from the reaction of <alpha>,<beta>-unsaturated aldehydes and nitroethanol.
2. As an extension of the above results, the first total synthesis of cerebroside B_<1b>, 4, which was isolated from Tetragonia tetragonoides as a principle withanti-ulcerogenic activity, was succeeded.
3. Optically active <alpha>-hydroxypalmitic acid 6 was synthesized by use of oxazolidinone 5.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (5 results)

All Other

All Publications (5 results)

  • [Publications] Tohru Hino: Journal of Chemical Society,Perkin Trans.1. 1687-1690 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Masako Nakagawa: Tetrahedron Letters. 28. 6281-6284 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Tohru Hino, Kiyoshi Nakayama, Mikio Taniguchi, and Masako Nakagawa: "A New Route to Racemic erythro-Sphingosine and Ceramides. The 1,2-versus 1,4-Addition Reaction of Hexadec-2-enal with 2-Nitroethanol" Jouranl of Chemcal Society, Perkin Trans. 1.1687-1690 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Masako Nakagawa, Shin-ichi Kodato, Kiyoshi Nakayama, Tohru Hino: "Total Synthesis and Determination of Absolute Configuration of Cerebroside B_<1b> and Its Stereoisomers." Tetrahedron Letters. 28. 6281-6284 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T.Hino;K.Nakayama;M.Taniguchi;M.Nakagawa: Journal ehemical Society,Perkin Transactions I. 1687-1690 (1986)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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