methyl (S,E)-7-[(1S,2R,3R,5S)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate | 1025719-24-7

• 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: methyl (S,E)-7-[(1S,2R,3R,5S)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate
• 英文别名: methyl (E,5S)-7-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(2-hydroxyethyl)cyclopentyl]-5-[tert-butyl(dimethyl)silyl]oxyhept-6-enoate
• CAS: 1025719-24-7
• 化学式: C₃₃H₆₈O₆Si₃
• 分子量: 645.156
• InChiKey: QHPSDAWZQISNJP-WHCUXKOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.08
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S,E)-7-[(1S,2R,3R,5S)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  由肾上腺酸和 EPA 衍生的异前列烷的全合成

  摘要：

  已经合成了富含对映异构体的 F2-二高异前列腺素和 F3 异前列腺素。此类化合物分别源自活性氧对磷脂结合的多不饱和脂肪酸 (PUFA)、肾上腺酸和二十碳五烯酸的作用。特别令人感兴趣的是 F2-二高异前列腺素，因为它们可以代表髓鞘损伤的潜在生物标志物，因为其主要 PUFA 成分是肾上腺酸。我们的策略基于关键的对映异构体富集中间体，首次允许访问 F2-dihomo-IsoP 和 5-F3t-IsoP 的两个 C5 差向异构体。

  DOI：

  10.1002/ejoc.201200070
• 作为产物：
  描述：

  在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以112 mg的产率得到methyl (S,E)-7-[(1S,2R,3R,5S)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate
  参考文献：
  名称：

  A Cross-Metathesis Route to the 5-F₂-Isoprostanes

  摘要：

  A library of eight 5-F-2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and alpha,beta-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F-2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.

  DOI：

  10.1021/jo702702s

文献信息

• A Cross-Metathesis Route to the 5-F₂-Isoprostanes
  作者：Bhaumik A. Pandya、Marc L. Snapper

  DOI：10.1021/jo702702s

  日期：2008.5.1

  A library of eight 5-F-2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and alpha,beta-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F-2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.
• Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA
  作者：Camille Oger、Valérie Bultel-Poncé、Alexandre Guy、Thierry Durand、Jean-Marie Galano

  DOI：10.1002/ejoc.201200070

  日期：2012.5

  been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid-bound polyunsaturated fatty acids (PUFA), adrenic acid and eicosapentaenoic acid, respectively. Of special interest are the F2-dihomo-isoprostanes because they could represent potential biomarkers for myelin damage as its main PUFA constituent is adrenic acid. Our strategy, based on a pivotal enantiomerically

  已经合成了富含对映异构体的 F2-二高异前列腺素和 F3 异前列腺素。此类化合物分别源自活性氧对磷脂结合的多不饱和脂肪酸 (PUFA)、肾上腺酸和二十碳五烯酸的作用。特别令人感兴趣的是 F2-二高异前列腺素，因为它们可以代表髓鞘损伤的潜在生物标志物，因为其主要 PUFA 成分是肾上腺酸。我们的策略基于关键的对映异构体富集中间体，首次允许访问 F2-dihomo-IsoP 和 5-F3t-IsoP 的两个 C5 差向异构体。