(5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoic acid | 1158076-92-6

• 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: (5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoic acid
• CAS: 1158076-92-6
• 化学式: C₂₃H₃₀O₃Si
• 分子量: 382.575
• InChiKey: DWULWHXDDFLKJJ-LJQANCHMSA-N

物化性质

• 沸点：
  466.7±45.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4-烯基-2-戊醇 、 (5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(1R)-1-methyl-3-butenyl (5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoate
  参考文献：
  名称：

  Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation

  摘要：

  The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2008.12.002
• 作为产物：
  描述：

  (5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-hepten-1-ol 在 pyridinium dichromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以75%的产率得到(5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoic acid
  参考文献：
  名称：

  Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation

  摘要：

  The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2008.12.002