(8E,10E)-methyl 5(S),12(R)-bis(tert-butyldiphenylsiloxy)eicosa-8,10-diene-14,16-diynoate | 90108-34-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (8E,10E)-methyl 5(S),12(R)-bis(tert-butyldiphenylsiloxy)eicosa-8,10-diene-14,16-diynoate
• 英文别名: (5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate；methyl (5S,8E,10E,12R)-5,12-bis[[tert-butyl(diphenyl)silyl]oxy]icosa-8,10-dien-6,14-diynoate
• CAS: 90108-34-2
• 化学式: C₅₃H₆₆O₄Si₂
• 分子量: 823.276
• InChiKey: XMBXNGXLQLTPHX-LAVPYQDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8E,10E)-methyl 5(S),12(R)-bis(tert-butyldiphenylsiloxy)eicosa-8,10-diene-14,16-diynoate 在 10% palladium on barium sulfate 吡啶 、 喹啉 、 lithium hydroxide 、 氢氟酸 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 29.0h， 生成 白三烯B4
  参考文献：
  名称：

  Total synthesis of leukotriene B4

  摘要：

  A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.

  DOI：

  10.1021/jo00065a012
• 作为产物：
  描述：

  (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal 在 lithium hexamethyldisilazane 作用下， 以 苯 为溶剂， 反应 19.0h， 生成 (8E,10E)-methyl 5(S),12(R)-bis(tert-butyldiphenylsiloxy)eicosa-8,10-diene-14,16-diynoate
  参考文献：
  名称：

  Total synthesis of leukotriene B4

  摘要：

  A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.

  DOI：

  10.1021/jo00065a012

文献信息

• A general and stereocontrolled total synthesis of leukotriene B4 and analogs
  作者：K. C. Nicolaou、R. E. Zipkin、R. E. Dolle、B. D. Harris

  DOI：10.1021/ja00324a024

  日期：1984.6
• J. Org. Chem. 1993, 58, 3516-3520
  作者：

  DOI：——

  日期：——
• Total synthesis of leukotriene B4
  作者：Francis A. J. Kerdesky、Steven P. Schmidt、Dee W. Brooks

  DOI：10.1021/jo00065a012

  日期：1993.6

  A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.