7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid | 87007-31-6

• 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)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid
• 英文别名: 7-[(1R,2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
• CAS: 87007-31-6
• 化学式: C₃₂H₆₂O₅Si₂
• 分子量: 583.012
• InChiKey: MVNOEICXKZDREW-DYMPWYIUSA-N

物化性质

• 沸点：
  599.7±50.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

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)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid 在 氢氟酸 作用下， 以 乙腈 为溶剂， 生成 前列地尔
  参考文献：
  名称：

  Prostaglandin synthesis via two-component coupling. Highly efficient synthesis of chiral prostaglandin intermediates 4-alkoxy-2-alkyl-2-cyclopenten-1-one and 4-alkoxy-3-alkenyl-2-methylenecyclopentan-1-one

  摘要：

  DOI：

  10.1021/jo00258a051
• 作为产物：
  描述：

  (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene 在 chromium(VI) oxide 、 4-甲基苯磺酸吡啶 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid
  参考文献：
  名称：

  Prostaglandin synthesis via two-component coupling. Highly efficient synthesis of chiral prostaglandin intermediates 4-alkoxy-2-alkyl-2-cyclopenten-1-one and 4-alkoxy-3-alkenyl-2-methylenecyclopentan-1-one

  摘要：

  DOI：

  10.1021/jo00258a051

文献信息

• A biogenetically patterned total synthesis of prostaglandin E1
  作者：Chisato Sato、Shun'ichi Ikeda、Haruhisa Shirahama、Takeshi Matsumoto

  DOI：10.1016/s0040-4039(00)87271-8

  日期：1982.1

  Methyl 11-tert-butyldimethylsilyloxyeicosa-8(Z), 12(E), 14(E)-trienoate was stereoselectively cyclized by treatment with Hg(OCOCF3)2 to give a properly functionalized PG skeleton, which was converted to PGE1 in good over all yield.

  甲基-11-叔butyldimethylsilyloxyeicosa-8（Z），12（E），14（E）是-trienoate立体选择性地通过环化处理用汞（OCOCF 3）2，得到适当官能化PG骨架，将其转化为PGE 1在整体产量高。
• A highly efficient approach to prostaglandins via radical addition of α side-chains to methylenecyclopentanones. Total synthesis of natural PGE1, limaprost and new prostaglandin derivatives.
  作者：Naoya Ono、Yukio Yoshida、Kousuke Tani、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/0040-4039(93)85062-2

  日期：1993.10

  Reaction of methylenecyclopentanones2 with alkyl iodides via radical 1,4-addition pathway proceeds in good yields, thus providing an easy method for synthesis of not only known prostaglandins such as PGE1 and Limafrost but also new prostaglandin derivatives.

  亚甲基环戊酮2通过自由基1,4-加成途径与烷基碘的反应以良好的收率进行，因此不仅为已知的前列腺素（如PGE 1和利马弗罗斯特）而且为新的前列腺素衍生物的合成提供了简便的方法。
• Synthesis of Allyl Ester of Prostaglandin E and the Conversion of the Allyl Ester Moiety into Carboxylic Acid by Chemical Method. A Highly Practical Synthesis of Natural PGE₁and Limaprost
  作者：Naoya Ono、Mie Tsuboi、Sentaro Okamoto、Tohru Tanami、Fumie Sato

  DOI：10.1246/cl.1992.2095

  日期：1992.10

  Synthesis of prostaglandin E allyl ester via two-component coupling process and the conversion of the allyl ester moiety into free carboxylic acid by the reaction with HCO2H-Et3N in the presence of a palladium catalyst has been described.

  已经描述了通过双组分偶联方法合成前列腺素 E 烯丙酯和在钯催化剂存在下通过与 HCO2H-Et3N 反应将烯丙酯部分转化为游离羧酸。
• The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost
  作者：Giuseppe Zanoni、Alessandro D’Alfonso、Alessio Porta、Lazzaro Feliciani、Steven P. Nolan、Giovanni Vidari

  DOI：10.1016/j.tet.2010.07.069

  日期：2010.9

  Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.
• NOERI, REDZI;SUDZUKI, MASAAKI;KAVATISI, TOSIO;KURODZUMI, SEHJDZI
  作者：NOERI, REDZI、SUDZUKI, MASAAKI、KAVATISI, TOSIO、KURODZUMI, SEHJDZI

  DOI：——

  日期：——