(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester | 177768-48-8

• 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)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
• 英文别名: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(2S,3S)-3-[(1R)-1-hydroxy-3-phenylpropyl]oxiran-2-yl]cyclopentyl]hept-5-enoate
• CAS: 177768-48-8
• 化学式: C₂₆H₃₈O₆
• 分子量: 446.584
• InChiKey: SAPVYHNEZAWFQE-BPIISEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester 在 lithium hydroxide 、 双氧水 、 苯硼酸 作用下， 生成 (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((1R,2S,3R)-1,2,3-trihydroxy-5-phenyl-pentyl)-cyclopentyl]-hept-5-enoic acid isopropyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Reactions of 17-Phenyl-18,19,20-trinorprostaglandin F_2α Isopropyl Ester

  摘要：

  Novel prostaglandin F-2 alpha derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F-2 alpha isopropyl ester [(15S)-1] and its epimer [(15R)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.

  DOI：

  10.1021/jo960098t
• 作为产物：
  描述：

  (Z)-7-[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 sodium hydrogen sulfate 、 三氯化铝 、 cerium(III) chloride 、 (-)-diisopropyl tartrate 、 3 A molecular sieve 、 双氧水 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 lithium chloride 、 苯硼酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.5h， 生成 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Reactions of 17-Phenyl-18,19,20-trinorprostaglandin F_2α Isopropyl Ester

  摘要：

  Novel prostaglandin F-2 alpha derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F-2 alpha isopropyl ester [(15S)-1] and its epimer [(15R)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.

  DOI：

  10.1021/jo960098t