(5Z,8Z,11Z,13E,15E,17S,18S)-17,18-bis((tert-butyldimethylsilyl)oxy)icosa-5,8,11,13,15-pentaenoic acid | 1360805-97-5

• 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: (5Z,8Z,11Z,13E,15E,17S,18S)-17,18-bis((tert-butyldimethylsilyl)oxy)icosa-5,8,11,13,15-pentaenoic acid
• CAS: 1360805-97-5
• 化学式: C₃₂H₅₈O₄Si₂
• 分子量: 562.981
• InChiKey: CPDRCLAJCODOAK-AYRGAIPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.99
• 重原子数：
  38.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,13E,15E,17S,18S)-17,18-bis((tert-butyldimethylsilyl)oxy)icosa-5,8,11,13,15-pentaenoic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (17S,18S)-resolvin E3
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045
• 作为产物：
  描述：

  (5S,6S)-5-((1E,3E,5Z,8Z,11Z)-15-(1,3-dioxolan-2-yl)pentadeca-1,3,5,8,11-pentaen-1-yl)-6-ethyl-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane 在 2,6-二甲基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (5Z,8Z,11Z,13E,15E,17S,18S)-17,18-bis((tert-butyldimethylsilyl)oxy)icosa-5,8,11,13,15-pentaenoic acid
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045