(Z)-7-{(1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester | 443796-77-8

• 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,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester
• CAS: 443796-77-8
• 化学式: C₃₅H₆₆O₅Si₂
• 分子量: 623.077
• InChiKey: PVVIXEONPHUWMZ-JESYJLAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.58
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-{(1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 在 sodium hydroxide 、 氢氟酸 、 四丁基氯化铵 作用下， 以 吡啶 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 生成 (Z)-7-{(1R,2R,3R,5S)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00008-1
• 作为产物：
  描述：

  (Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 在 ammonium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 (Z)-7-{(1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00008-1