{2-[1-(2,4-Dimethoxy-benzyl)-2,4-dioxo-pyrrolidin-(3E)-ylidene]-2-hydroxy-ethyl}-phosphonic acid diethyl ester | 137628-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {2-[1-(2,4-Dimethoxy-benzyl)-2,4-dioxo-pyrrolidin-(3E)-ylidene]-2-hydroxy-ethyl}-phosphonic acid diethyl ester
• CAS: 137628-50-3
• 化学式: C₁₉H₂₆NO₈P
• 分子量: 427.391
• InChiKey: DHCZSVZQQSHBHF-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111.6
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {2-[1-(2,4-Dimethoxy-benzyl)-2,4-dioxo-pyrrolidin-(3E)-ylidene]-2-hydroxy-ethyl}-phosphonic acid diethyl ester 、 (E)-(S)-4-((1R,2R,4S,6R,7S,8S)-1,7-Dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-2-methyl-pent-2-enal 在 potassium tert-butylate 作用下， 生成 1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione
  参考文献：
  名称：

  A total synthesis of (.+-.)-tirandamycin B

  摘要：

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.

  DOI：

  10.1021/ja00023a029