Synthesis of 2-amino alcohol derivatives oriented for a potent sphingomyelinase inhibitor

DOI

Bibliographic Information

Other Title
  • SMase阻害剤を指向した新規SMA-7類縁体の合成研究

Description

Various alpha-amino ketones bearing a difluoromethylenephosphonate (DFMP) group at beta-position was synthesized by Liebeskind-Srogl reaction from the thioester of alpha-amino acid derivatives with boronic acids. Reduction of the obtained alpha-amino ketones with LiAlH(OtBu)3 proceeded in excellent diastereoselectivity to give anti-amino alcohols. These alcohol derivatives were readily converted into gamma-palmitoylamino-delta-hydroxy-alpha,alpha-difluorophosphonate, which would be useful as a vehicle for structure-activity relationship (SAR) studies on SMA-7, a potent spingomyelinase inhibitor. This synthetic method features high diversity and efficiency in replacement of the terminal substituent of SMA-7 for SAR studies.

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Keywords

Details 詳細情報について

  • CRID
    1390282680612484224
  • NII Article ID
    130006998328
  • DOI
    10.14895/hannou.35.0.109.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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