1-[(3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]oct-2-ynyl acetate | 1251949-10-6

• 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: 1-[(3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]oct-2-ynyl acetate
• CAS: 1251949-10-6
• 化学式: C₂₃H₃₈O₅Si
• 分子量: 422.637
• InChiKey: AKKOZYRXFQABAZ-XFMLVYLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]oct-2-ynyl acetate 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) 、 叔丁醇 作用下， 以 水 、 丁酮 为溶剂， 反应 36.0h， 以95%的产率得到3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
  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
• 作为产物：
  描述：

  5-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-2-氧代六氢-2H-环戊二烯并[b]呋喃-4-甲醛 、 1-庚炔 、 乙酸酐 在 正丁基锂 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到1-[(3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]oct-2-ynyl acetate
  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