(3S,5S)-(-)-[5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidin-5-yl]methanol | 1050517-99-1

• 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: (3S,5S)-(-)-[5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidin-5-yl]methanol
• 英文别名: 5-fluoro-1-[(3S,5S)-5-(hydroxymethyl)-2-methyl-3-phenyl-1,2-oxazolidin-5-yl]pyrimidine-2,4-dione
• CAS: 1050517-99-1
• 化学式: C₁₅H₁₆FN₃O₄
• 分子量: 321.308
• InChiKey: RDKXHIHAADOSMS-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (3S,5S)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-3-phenylisoxazolidine-5-carboxylate 在 红铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以61%的产率得到(3S,5S)-(-)-[5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)-2-methyl-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

文献信息

• Synthesis and Absolute Configuration of Novel <i>N</i>,<i>O</i>-Psiconucleosides Using (<i>R</i>)-<i>N</i>-Phenylpantolactam as a Resolution Agent
  作者：Pelayo Camps、Tània Gómez、Diego Muñoz-Torrero、Jordi Rull、Laura Sánchez、Francesca Boschi、Mauro Comes-Franchini、Alfredo Ricci、Teresa Calvet、Mercè Font-Bardia、Erik De Clercq、Lieve Naesens

  DOI：10.1021/jo800769m

  日期：2008.9.1

  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.