16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether) | 256382-46-4

• 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: 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)
• 英文别名: methyl 4-[2-[(1R,2R,3R)-2-[(E,3S)-4-[3-(methoxymethyl)phenyl]-3-(oxan-2-yloxy)but-1-enyl]-3-(oxan-2-yloxy)-5-oxocyclopentyl]ethylsulfanyl]butanoate
• CAS: 256382-46-4
• 化学式: C₃₄H₅₀O₈S
• 分子量: 618.832
• InChiKey: NBHYVZUXYXPJTM-DGEBVRPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether) 在 盐酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 以74.2%的产率得到甲基4-({2-[(1R,2R,3S)-3-羟基-2-{(1E)-3-羟基-4-[3-(甲氧基甲基)苯基]-1-丁烯-1-基}-5-氧代环戊基]乙基}硫基)丁酸酯
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 4: practical synthesis and biological evaluation of a novel highly selective EP4-receptor agonist

  摘要：

  A practical method of synthesizing it highly selective EP4-receptor agonist 1 using Corey lactone 2 as a key intermediate was developed. Selective methanesulfonylation of the primary alcohol of the diol 8 under the newly devised conditions followed by the protection of the remaining secondary alcohol are key reactions in this new method. Further biological evaluation of 1a-b is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00085-8
• 作为产物：
  描述：

  6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one 在 lithium aluminium tetrahydride 、 pyridine-SO3 complex 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 4: practical synthesis and biological evaluation of a novel highly selective EP4-receptor agonist

  摘要：

  A practical method of synthesizing it highly selective EP4-receptor agonist 1 using Corey lactone 2 as a key intermediate was developed. Selective methanesulfonylation of the primary alcohol of the diol 8 under the newly devised conditions followed by the protection of the remaining secondary alcohol are key reactions in this new method. Further biological evaluation of 1a-b is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00085-8

文献信息

• Design and synthesis of a selective EP4-receptor agonist. Part 4: practical synthesis and biological evaluation of a novel highly selective EP4-receptor agonist
  作者：Toru Maruyama、Shin-Itsu Kuwabe、Yasufumi Kawanaka、Tai Shiraishi、Yoshiyuki Shinagawa、Kiyoto Sakata、Akiteru Seki、Yoko Kishida、Hideyuki Yoshida、Takayuki Maruyama、Shuichi Ohuchida、Hisao Nakai、Shinsuke Hashimoto、Masanori Kawamura、Kigen Kondo、Masaaki Toda

  DOI：10.1016/s0968-0896(02)00085-8

  日期：2002.7

  A practical method of synthesizing it highly selective EP4-receptor agonist 1 using Corey lactone 2 as a key intermediate was developed. Selective methanesulfonylation of the primary alcohol of the diol 8 under the newly devised conditions followed by the protection of the remaining secondary alcohol are key reactions in this new method. Further biological evaluation of 1a-b is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.