(3aS,4R,5S,6aR)-2-oxo-5-triethylsilyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde | 186794-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,4R,5S,6aR)-2-oxo-5-triethylsilyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde
• CAS: 186794-83-2
• 化学式: C₁₄H₂₄O₄Si
• 分子量: 284.428
• InChiKey: REQGGRBXTCRVDB-LOWDOPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,6aR)-2-oxo-5-triethylsilyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 (3aS,4R,5S,6aR)-4-[(E,3R)-3-hydroxyoct-1-enyl]-5-triethylsilyloxy-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  Roland, Arlene; Durand, Thierry; Rondott, Benoit, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 11, p. 1149 - 1154

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4S,5S,6aR)-5-Triethylsilanyloxy-4-triethylsilanyloxymethyl-hexahydro-cyclopenta[b]furan-2-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3aS,4R,5S,6aR)-2-oxo-5-triethylsilyloxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde
  参考文献：
  名称：

  Eicosapentaenoic-acid-derived isoprostanes: Synthesis and discovery of two major isoprostanes

  摘要：

  The stereospecific synthesis of two all-syn-EPA-derived isoprostanes (iPs), 5-epi-8,12-iso-iPF(3 alpha)-VI 17 and 8,12-iso-iPF(3 alpha)-VI 18, has been accomplished. These two synthetic probes have been used to discover and identify their presence in human urine. The eventual quantitative measurement of these two iPs may be a valuable index of oxidative stress in people with eicosapentaenoic acid-(EPA) and docosahexaenoic acid-(DHA) enriched phospholipids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.008

文献信息

• A new approach to the synthesis of polyunsaturated deuterated isoprostanes: Total synthesis of d4-5-epi-8,12-iso-iPF3α-VI and d4-8,12-iso-iPF3α-VI
  作者：Chih-Tsung Chang、Pranav Patel、Vivek Gore、Wen-Liang Song、John A. Lawson、William S. Powell、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/j.bmcl.2009.09.099

  日期：2009.12

  The total and stereospecific synthesis of d(4)-5-epi-8,12-iso-iPF(3 alpha)-VI 55 and d(4)-8,12-iso-iPF(3 alpha)-VI 64, EPA-derived all-syn-isoprostanes (iPs), has been accomplished. Because of issues related to volatility and yield with some of the primary deuterated synthons an improved synthesis is presented. These two deuterated analogs were used to discover and quantify the presence of the corresponding endogenous isoprostanes in human urine. These assays may serve as a valuable index of oxidative stress in population with omega-3 fatty acid enriched diets containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and may also be useful as an index of the severity of inflammatory diseases such as atherosclerosis and Alzheimer's disease. (C) 2009 Elsevier Ltd. All rights reserved.