(Z)-7-((1R,2R,3R,5S)-5-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-3-hydroxycyclopentyl)hept-5-enoic acid | 64767-24-4

• 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: (Z)-7-((1R,2R,3R,5S)-5-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-3-hydroxycyclopentyl)hept-5-enoic acid
• CAS: 64767-24-4
• 化学式: C₃₂H₆₂O₅Si₂
• 分子量: 583.012
• InChiKey: QYJWUNBCSRBQGO-ONGNOKONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 、 5β-(dimethyl-t-butylsilyloxy)-4α-<<(E),(3S)>-3-(dimethyl-t-butylsilyloxy)oct-1-enyl>-cis-(3aαH,6aαH)-perhydrocyclopentafuran-2-ol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以107 mg的产率得到(Z)-7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoic acid
  参考文献：
  名称：

  The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

  摘要：

  Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.069