(E)-(R)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-cyclopentyl]-oct-1-en-3-ol | 470700-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-(R)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-cyclopentyl]-oct-1-en-3-ol
• 英文别名: (E,3R)-1-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(2-hydroxyethyl)cyclopentyl]oct-1-en-3-ol
• CAS: 470700-53-9
• 化学式: C₂₇H₅₆O₄Si₂
• 分子量: 500.91
• InChiKey: KZRKSBSRTIVQGB-SLILXDRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(R)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-cyclopentyl]-oct-1-en-3-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 N-氯代丁二酰亚胺 、 四丁基氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.2h， 以82%的产率得到
  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
• 作为产物：
  描述：

  (E)-1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-ol 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以62.5 mg的产率得到(E)-(R)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-ethyl)-cyclopentyl]-oct-1-en-3-ol
  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