Stereoselective synthesis of threo-4,4,4-trichlorothreonine.

DOI
  • MATSUMOTO Kazuo
    Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
  • URABE Yuji
    Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
  • OZAKI Yasuhiko
    Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
  • IWASAKI Tameo
    Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
  • MIYOSHI Muneji
    Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

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説明

threo-4, 4, 4-Trichlorothreonine was synthesized completely stereoselectively through trans-4-alkoxycarbonyl-5-trichloromethyl-2-oxazoline, which was prepared almost quantitatively by the reaction of 2-isocyano acetate with chloral in the presence of an organic base. Several derivatives of these compounds were also synthesized.<br> Furthermore, the stereochemistry of the resulting trichlorocompounds was chemically elucidated. The trichlorothreonine was easily converted into threo-threonine by hydrogenation over Pd/C in the presence of NaHCO3.

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詳細情報 詳細情報について

  • CRID
    1390001206472304000
  • NII論文ID
    130003525101
  • DOI
    10.1271/bbb1961.39.1869
  • COI
    1:CAS:528:DyaE2MXlsl2mt78%3D
  • ISSN
    18811280
    00021369
  • 本文言語コード
    en
  • データソース種別
    • JaLC
    • Crossref
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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