[(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate | 195196-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate
• CAS: 195196-19-1
• 化学式: C₄₁H₆₁NO₄Si₂
• 分子量: 688.111
• InChiKey: OVIFKZDPNNDDQD-VDSGVDATSA-N

物化性质

• 沸点：
  666.9±55.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.39
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate 在 palladium dihydroxide 氢氟酸 、 氢气 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 生成 (2S,3S)-2-羟基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-3-苯丙酸
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v
• 作为产物：
  描述：

  (R)-n-(α-甲基苄基)羟胺草酸盐 在 碳酸氢钠 、 magnesium sulfate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v

文献信息

• Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2<i>S</i>,3<i>S</i>)-<i>N</i>-Benzoyl- and <i>N</i>-Boc-phenylisoserine
  作者：Sylvie Jost、Yves Gimbert、Andrew E. Greene、Frédéric Fotiadu

  DOI：10.1021/jo971009v

  日期：1997.9.1

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.