(Z)-7-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid | 470700-81-3

• 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-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid
• CAS: 470700-81-3
• 化学式: C₃₂H₆₂O₅Si₂
• 分子量: 583.012
• InChiKey: JKCFVZWUATXGIS-WNTFOVKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 [(2R)-2-[(Z)-7-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[methoxy-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]phosphoryl]oxypropyl] hexadecanoate
  参考文献：
  名称：

  Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

  摘要：

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.

  DOI：

  10.1021/jo0518553
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 、 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以31.0 mg的产率得到(Z)-7-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid
  参考文献：
  名称：

  Stereodivergent Synthesis of All 15-F₂ Isoprostanes

  摘要：

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.

  DOI：

  10.1021/ja027154u