(2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylsulfanyl-2H-furan-5-one | 144728-51-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylsulfanyl-2H-furan-5-one
• CAS: 144728-51-8
• 化学式: C₂₇H₂₈O₃SSi
• 分子量: 460.669
• InChiKey: WRQLTDXQFGNBSA-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lithium diphenyl cuprate 、 (2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylsulfanyl-2H-furan-5-one 反应 1.0h， 以94%的产率得到(3S,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenyl-3-phenylsulfanyloxolan-2-one
  参考文献：
  名称：

  Suppression of racemization during the diastereoselective C-3 functionalization of 5-hydroxymethyl-2-phenylthio-2-(5H)-furanones

  摘要：

  The methodology described herein examines the enantio- and stereoselective C-3 functionalization of 5-hydroxymethyl-2-(5H)-furanones via 1, 4-organocuprate addition as well as the involvement of temperature and TMSCl in the selectivity. The results imply that reactions carried out at -78-degrees-C and those carried out at 0-degrees-C to R.T. in the presence of TMSCl exhibit both high diastereoselection and enantioselection.

  DOI：

  10.1016/0040-4039(92)89006-x
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 六甲基磷酰三胺 、 磺酰氯 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 生成 (2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylsulfanyl-2H-furan-5-one
  参考文献：
  名称：

  Suppression of racemization during the diastereoselective C-3 functionalization of 5-hydroxymethyl-2-phenylthio-2-(5H)-furanones

  摘要：

  The methodology described herein examines the enantio- and stereoselective C-3 functionalization of 5-hydroxymethyl-2-(5H)-furanones via 1, 4-organocuprate addition as well as the involvement of temperature and TMSCl in the selectivity. The results imply that reactions carried out at -78-degrees-C and those carried out at 0-degrees-C to R.T. in the presence of TMSCl exhibit both high diastereoselection and enantioselection.

  DOI：

  10.1016/0040-4039(92)89006-x

文献信息

• Suppression of racemization during the diastereoselective C-3 functionalization of 5-hydroxymethyl-2-phenylthio-2-(5H)-furanones
  作者：Julie A. Wurster、Lawrence J. Wilson、Gregory T. Morin、Dennis Liotta

  DOI：10.1016/0040-4039(92)89006-x

  日期：1992.9

  The methodology described herein examines the enantio- and stereoselective C-3 functionalization of 5-hydroxymethyl-2-(5H)-furanones via 1, 4-organocuprate addition as well as the involvement of temperature and TMSCl in the selectivity. The results imply that reactions carried out at -78-degrees-C and those carried out at 0-degrees-C to R.T. in the presence of TMSCl exhibit both high diastereoselection and enantioselection.