(1R,2S,5S)-1-(2-(benzyloxy)ethyl)-2-(3-((tertbutyldimethylsilyl)oxy)propyl)-5-(2-hydroxypropan-2-yl)-2-methylcyclopentanol | 1246189-63-8

• 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-(2-(benzyloxy)ethyl)-2-(3-((tertbutyldimethylsilyl)oxy)propyl)-5-(2-hydroxypropan-2-yl)-2-methylcyclopentanol
• CAS: 1246189-63-8
• 化学式: C₂₇H₄₈O₄Si
• 分子量: 464.761
• InChiKey: YSHZBXMVJFGMGD-HUROMRQRSA-N

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S)-1-(2-(benzyloxy)ethyl)-2-(3-((tertbutyldimethylsilyl)oxy)propyl)-5-(2-hydroxypropan-2-yl)-2-methylcyclopentanol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1R,2S,5S)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-1-(2-hydroxyethyl)-5-(2-hydroxypropan-2-yl)-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：

  (1R,2R,3S)-methyl 2-(2-(benzyloxy)ethyl)-3-(3-((tertbutyldimethylsilyl)oxy)propyl)-2-hydroxy-3-methylcyclopentanecarboxylate 、 甲基溴化镁 以 乙醚 为溶剂， 以100%的产率得到(1R,2S,5S)-1-(2-(benzyloxy)ethyl)-2-(3-((tertbutyldimethylsilyl)oxy)propyl)-5-(2-hydroxypropan-2-yl)-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