methyl (3S,5S)-(-)-2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidine-5-carboxylate | 1050517-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl (3S,5S)-(-)-2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidine-5-carboxylate
• 英文别名: methyl (3S,5S)-2-methyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenyl-1,2-oxazolidine-5-carboxylate
• CAS: 1050517-73-1
• 化学式: C₁₇H₁₉N₃O₅
• 分子量: 345.355
• InChiKey: NTQXBEYGWHKTJW-GUYCJALGSA-N

物化性质

• 密度：
  1.315±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3S,5S)-(-)-2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidine-5-carboxylate 在 红铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以58%的产率得到(3S,5S)-(-)-[2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidin-5-yl]methanol
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

  摘要：

  A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2.3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

  DOI：

  10.1021/jo800769m
• 作为产物：
  描述：

  甲醇 、 (3S,5S,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidine-5-carboxylate 在 potassium carbonate 作用下， 反应 3.0h， 以75%的产率得到methyl (3S,5S)-(-)-2-methyl-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-3-phenylisoxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

  摘要：

  A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2.3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

  DOI：

  10.1021/jo800769m