(1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methylcyclopentanol | 1246189-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methylcyclopentanol
• CAS: 1246189-68-3
• 化学式: C₂₈H₄₈O₅Si
• 分子量: 492.772
• InChiKey: VLUYWGFYIJUARH-KWNVVKLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methylcyclopentanol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以67%的产率得到(1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-methylcyclopentanol
  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：

  、 (2-bromomethylallyloxymethyl)benzene 在 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 、 (1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methylcyclopentanol 、 (1R,2S,5S)-1-(3-((benzyloxy)methyl)-1-hydroxybut-3-en-1-yl)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methylcyclopentanol
  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