(3aS,4S,5S,6aR)-4-(hydroxymethyl)-5-((triethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one | 1092102-41-4

• 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,4S,5S,6aR)-4-(hydroxymethyl)-5-((triethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS: 1092102-41-4
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: IZGGSEPXQZJWBP-LOWDOPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5S,6aR)-4-(hydroxymethyl)-5-((triethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one 、 1-苯基-5-巯基四氮唑 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以97%的产率得到(3aS,4R,5S,6aR)-4-(((1-phenyl-1H-tetrazol-5-yl)thio)methyl)-5-((triethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
  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
• 作为产物：
  描述：

  (3aS,4S,5S,6aR)-5-Triethylsilanyloxy-4-triethylsilanyloxymethyl-hexahydro-cyclopenta[b]furan-2-one 在 Wilkinson's catalyst 、 儿萘酚硼烷 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(3aS,4S,5S,6aR)-4-(hydroxymethyl)-5-((triethylsilyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
  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