propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate | 1219097-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate
• CAS: 1219097-68-3
• 化学式: C₂₇H₃₀F₃NO₆S
• 分子量: 553.6
• InChiKey: WNMXCZMUBQDQRT-XZDHIHRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 、 PF-04475270
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092
• 作为产物：
  描述：

  propan-2-yl 5-[3-[(2S)-2-[(3R,4R)-3,4-dihydroxy-4-[3-(trifluoromethyl)phenyl]butyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092

文献信息

• Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation
  作者：Sajiv K. Nair、Jean J. Matthews、Stephan J. Cripps、Chunrong Ma、Elena Z. Dovalsantos、Alan W. Grubbs、Neal W. Sach、Wolter ten Hoeve、Han Koster、Erik J. Flahive、Steven P. Tanis、Matt Renner、Jim van Wiltenburg

  DOI：10.1016/j.tetlet.2009.12.092

  日期：2010.3

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.