(5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one | 129778-50-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one
• CAS: 129778-50-3；129778-55-8；142562-44-5
• 化学式: C₂₇H₃₀O₃SSi
• 分子量: 462.685
• InChiKey: HJJSFJSRHLYNSS-BWDMCYIDSA-N

物化性质

• 沸点：
  567.7±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one 在 三甲基氯硅烷 、 磺酰氯 、 zinc(II) chloride 作用下， 反应 14.0h， 生成
  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 、 二苯二硫醚 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 (5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-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

文献信息

• WILSON, LAWRENCE J.;LIOTTA, DENNIS, TETRAHEDRON LETT., 31,(1990) N3, C. 1815-1818
  作者：WILSON, LAWRENCE J.、LIOTTA, DENNIS

  DOI：——

  日期：——