{(1R,2R,3S)-3-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-hydroxy-cyclohexyl}-methyl-carbamic acid benzyl ester | 215116-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: {(1R,2R,3S)-3-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-hydroxy-cyclohexyl}-methyl-carbamic acid benzyl ester
• CAS: 215116-16-8
• 化学式: C₂₆H₄₂N₂O₅Si
• 分子量: 490.715
• InChiKey: XLZREGNMGPOMLV-UTZDURCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  90.31
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(1R,2R,3S)-3-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-hydroxy-cyclohexyl}-methyl-carbamic acid benzyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到{(1R,2R,3S)-2-Hydroxy-3-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-cyclohexyl}-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  Determination of the absolute configuration of an unexpectedly stable N-silylated isomer isolated en route to the trinem antibiotic GV129606

  摘要：

  The unexpected (3S,4R)-3-[(R)-1-(hydroxy)ethyl]-4-[(2'R,6'S)-1'-oxo-2'-(N-benzyloxy-N-methyl)aminocyclohexen-6'-yl]-1-(t-butyl-dimethylsilyl)azetidin-2-one was one of the main reaction products of the Lewis acid catalysed condensation of (3S,4R)-3-[(R)-1-(t-butyl-dimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one with 1-trimethylsilyloxy-6-(N-benzyloxycarbonyl-N-methylamino)cyclohexene. Its absolute configuration was established by NMR experiments on the corresponding, conformationally rigid, acetonide derivative. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00310-3
• 作为产物：
  描述：

  {(1R,3S)-3-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-oxo-cyclohexyl}-methyl-carbamic acid benzyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以75%的产率得到{(1R,2R,3S)-3-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-hydroxy-cyclohexyl}-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  Determination of the absolute configuration of an unexpectedly stable N-silylated isomer isolated en route to the trinem antibiotic GV129606

  摘要：

  The unexpected (3S,4R)-3-[(R)-1-(hydroxy)ethyl]-4-[(2'R,6'S)-1'-oxo-2'-(N-benzyloxy-N-methyl)aminocyclohexen-6'-yl]-1-(t-butyl-dimethylsilyl)azetidin-2-one was one of the main reaction products of the Lewis acid catalysed condensation of (3S,4R)-3-[(R)-1-(t-butyl-dimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one with 1-trimethylsilyloxy-6-(N-benzyloxycarbonyl-N-methylamino)cyclohexene. Its absolute configuration was established by NMR experiments on the corresponding, conformationally rigid, acetonide derivative. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00310-3