((1S,2R,3S)-1-acetoxymethyl-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-2-(2-hydroxyethyl)-3-methylcyclopentane) | 1246189-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: ((1S,2R,3S)-1-acetoxymethyl-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-2-(2-hydroxyethyl)-3-methylcyclopentane)
• CAS: 1246189-82-1
• 化学式: C₂₀H₄₀O₅Si
• 分子量: 388.62
• InChiKey: IFZVHXQGAVLJDH-DFQSSKMNSA-N

物化性质

• 沸点：
  435.1±10.0 °C(predicted)
• 密度：
  0.995±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((1S,2R,3S)-1-acetoxymethyl-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-2-(2-hydroxyethyl)-3-methylcyclopentane) 在 2-硝基苯基丝氰酸酯 、 三丁基膦 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以45.3 mg的产率得到(1S,2R,3S)-1-acetoxymethyl-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-3-methyl-2-vinylcyclopentane
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047
• 作为产物：
  描述：

  (1S,2R,3S)-1-acetoxymethyl-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-methylcyclopentane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ((1S,2R,3S)-1-acetoxymethyl-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-2-(2-hydroxyethyl)-3-methylcyclopentane)
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047