S-2-pyridyl 3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butanethioate | 141685-12-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-2-pyridyl 3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butanethioate
• 英文别名: S-pyridin-2-yl 3-[tert-butyl(dimethyl)silyl]oxybutanethioate
• CAS: 141685-12-3
• 化学式: C₁₅H₂₅NO₂SSi
• 分子量: 311.52
• InChiKey: NVLCQVXEFCYGFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  S-2-pyridyl 3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butanethioate 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 、 四氯化钛 、 三乙胺 作用下， 反应 2.58h， 生成 (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(hydroxymethyl)-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 sodium hydroxide 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 S-2-pyridyl 3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butanethioate
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019