((1S,2R,3S)-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-(((phenoxycarbonothioyl)oxy)methyl)cyclopentyl)methyl acetate | 1246189-79-6

• 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: ((1S,2R,3S)-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-(((phenoxycarbonothioyl)oxy)methyl)cyclopentyl)methyl acetate
• CAS: 1246189-79-6
• 化学式: C₃₄H₅₀O₇SSi
• 分子量: 630.918
• InChiKey: YIVOAJQHHGHTOQ-AQEWBBHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((1S,2R,3S)-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-(((phenoxycarbonothioyl)oxy)methyl)cyclopentyl)methyl acetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以72%的产率得到(1S,2R,3S)-1-acetoxymethyl-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-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
• 作为产物：
  描述：

  (1S,2R,3S)-1-acetoxymethyl-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-(hydroxymethyl)cyclopentane 、 硫代氯甲酸苯酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以90%的产率得到((1S,2R,3S)-2-(2-(benzyloxy)ethyl)-3-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-hydroxy-3-(((phenoxycarbonothioyl)oxy)methyl)cyclopentyl)methyl acetate
  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