7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester | 261772-00-3

• 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: 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
• CAS: 261772-00-3
• 化学式: C₃₇H₆₄O₆Si₂
• 分子量: 661.083
• InChiKey: GQSWWOPJXFXPDU-HIBFAQRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  45.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7
• 作为产物：
  描述：

  2-(S)-hydroxy-3-(3-methoxymethylphenyl)propan-1-ol trityl ether 在 咪唑 、 2,4,6-三甲基吡啶 、 sodium hydroxide 、 Schwartz's reagent 、 正丁基锂 、 草酰氯 、 水 、 叔丁基锂 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 7.33h， 生成 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7