(16RS)-5,6-didehydro-11-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsiloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester | 212311-34-7

• 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: (16RS)-5,6-didehydro-11-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsiloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester
• CAS: 212311-34-7
• 化学式: C₃₆H₆₄O₅Si₂
• 分子量: 633.072
• InChiKey: MRMRVLYURJJLBT-JSXKHEEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.63
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (16RS)-5,6-didehydro-11-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsiloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester 在 porcine liver esterase 、 ammonium sulfate 、 氢氟酸 作用下， 以 phosphate buffer 、 乙醇 、 乙腈 为溶剂， 反应 7.5h， 生成 7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-(1-propylcyclobutyl)but-1-enyl]-5-oxocyclopentyl]hept-5-ynoic acid
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives

  摘要：

  Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among those tested, 4a,b,e,f,h and 6a,b,e,f,h were found to be highly selective EP2-receptor agonists. Structure activity relationships are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00369-8
• 作为产物：
  描述：

  4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octyne 在 Schwartz's reagent 、 叔丁基锂 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 4.17h， 生成 (16RS)-5,6-didehydro-11-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsiloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives

  摘要：

  Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among those tested, 4a,b,e,f,h and 6a,b,e,f,h were found to be highly selective EP2-receptor agonists. Structure activity relationships are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00369-8