methyl (S)-5-((tert-butyldimethylsilyl)oxy)-5-((R)-2-oxo-1,3-dioxolan-4-yl)pentanoate | 1224702-16-2

• 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)-5-((tert-butyldimethylsilyl)oxy)-5-((R)-2-oxo-1,3-dioxolan-4-yl)pentanoate
• CAS: 1224702-16-2
• 化学式: C₁₅H₂₈O₆Si
• 分子量: 332.469
• InChiKey: HXJSGNXHLWJMKS-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-5-((tert-butyldimethylsilyl)oxy)-5-((R)-2-oxo-1,3-dioxolan-4-yl)pentanoate 在 甲醇 、 sodium methylate 作用下， 反应 20.0h， 生成 、
  参考文献：
  名称：

  Total synthesis of resolvin E2

  摘要：

  Resolvin E2 (2) was synthesized stereoselectively using the C1-8 and C15-20 aldehydes 6 and 9, which were connected to the C9-14 fragment by using Wittig reactions. The aldehyde 6 was prepared from the gamma-silyl alcohol (S)-20 by a sequence of reactions involving ozonolysis, oxidation with NalO(4), and the Wittig reaction of the resulting aldehyde with Ph3P=CHCHO, whereas the aldehyde 9 was synthesized from the corresponding gamma-silyl alcohol through epoxidation, reaction with Et2AlCN, and reduction with DIBAL-H. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.109
• 作为产物：
  描述：

  重氮甲烷 、 以92%的产率得到methyl (S)-5-((tert-butyldimethylsilyl)oxy)-5-((R)-2-oxo-1,3-dioxolan-4-yl)pentanoate
  参考文献：
  名称：

  Total synthesis of resolvin E2

  摘要：

  Resolvin E2 (2) was synthesized stereoselectively using the C1-8 and C15-20 aldehydes 6 and 9, which were connected to the C9-14 fragment by using Wittig reactions. The aldehyde 6 was prepared from the gamma-silyl alcohol (S)-20 by a sequence of reactions involving ozonolysis, oxidation with NalO(4), and the Wittig reaction of the resulting aldehyde with Ph3P=CHCHO, whereas the aldehyde 9 was synthesized from the corresponding gamma-silyl alcohol through epoxidation, reaction with Et2AlCN, and reduction with DIBAL-H. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.109