2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol | 69810-09-9

• 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: 2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol
• 英文别名: methyl (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-(2-methoxypropan-2-yloxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• CAS: 69810-09-9
• 化学式: C₂₃H₄₀O₇
• 分子量: 428.566
• InChiKey: DGTONZVAFXNRII-UJGFRWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 双氧水 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 24.91h， 生成 16-(4-chlorophenoxy)-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011
• 作为产物：
  描述：

  、 碘甲烷 以 丙酮 为溶剂， 反应 0.83h， 生成 2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011

文献信息

• Synthesis of a Highly Selective EP2-Receptor Agonist
  作者：Kousuke Tani、Atsushi Naganawa、Akiharu Ishida、Hiromu Egashira、Yoshihiko Odagaki、Toru Miyazaki、Tomoyuki Hasegawa、Yasufumi Kawanaka、Hisao Nakai、Shuichi Ohuchida、Masaaki Toda

  DOI：10.1055/s-2002-19781

  日期：——

  A practical method for the synthesis of the prostanoid EP2-receptor agonist 1 was developed. This method includes magnesium-mediated Julia olefination of aldehyde 2 with the optically active sulfone 3, which was prepared from allylic alcohol 4 using the Sharpless asymmetric epoxidation procedure.

  开发了一种合成前列腺素 EP2 受体激动剂 1 的实用方法。该方法包括使用 Sharpless 不对称环氧化程序从烯丙醇 4 制备醛 2 与旋光砜 3 的镁介导的 Julia 烯化。
• A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues
  作者：K Tani

  DOI：10.1016/s0968-0896(02)00008-1

  日期：2002.6

  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.