(3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether | 64072-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
• 英文别名: (3aR,4R,5R,6aS)-5-((tert-Butyldimethylsilyl)oxy)-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one；(3aR,4R,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 64072-30-6
• 化学式: C₂₁H₃₈O₄Si
• 分子量: 382.616
• InChiKey: XDIJVSIGMKPOKE-UOLDCSGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether 在 盐酸 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2H-环戊并[B]呋喃-2-酮,六氢-5-羟基-4-[(1E,3S)-3-羟基-1-辛烯-1-基]-,(3AR,4R,5R,6AS)-(...)
  参考文献：
  名称：

  Circular dichroism of prostaglandin benzoates. Assignment of configuration at C-15

  摘要：

  DOI：

  10.1021/jo01296a043
• 作为产物：
  描述：

  3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether 在 (-)-diisopinocamphenylborane chloride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以82%的产率得到(3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Gold-Catalyzed Meyer−Schuster Rearrangement: Application to the Synthesis of Prostaglandins

  摘要：

  DOI：

  10.1021/om1005534

文献信息

• The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost
  作者：Giuseppe Zanoni、Alessandro D’Alfonso、Alessio Porta、Lazzaro Feliciani、Steven P. Nolan、Giovanni Vidari

  DOI：10.1016/j.tet.2010.07.069

  日期：2010.9

  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.
• Cross Metathesis as a General Strategy for the Synthesis of Prostacyclin and Prostaglandin Analogues
  作者：Neil A. Sheddan、Johann Mulzer

  DOI：10.1021/ol061141u

  日期：2006.7.1

  [GRAPHICS]A cross metathesis ( CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF(2 alpha) and the formal syntheses of 15-deoxy-TIC and PGJ(2).
• Circular dichroism of prostaglandin benzoates. Assignment of configuration at C-15
  作者：Roy A. Johnson、William C. Krueger、Eldon G. Nidy、Loraine M. Pschigoda、Mary J. Garry

  DOI：10.1021/jo01296a043

  日期：1980.4
• Gold-Catalyzed Meyer−Schuster Rearrangement: Application to the Synthesis of Prostaglandins
  作者：Rubén S. Ramón、Sylvain Gaillard、Alexandra M. Z. Slawin、Alessio Porta、Alessandro D’Alfonso、Giuseppe Zanoni、Steven P. Nolan

  DOI：10.1021/om1005534

  日期：2010.8.23