tert-butyl (4S)-4-[(2R)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,3-oxazolidine-3-carboxylate | 1174408-08-2

• 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: tert-butyl (4S)-4-[(2R)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 1174408-08-2
• 化学式: C₁₇H₂₇N₃O₆
• 分子量: 369.418
• InChiKey: KOSNYFVDCURTES-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(2R)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,3-oxazolidine-3-carboxylate 在 platinum(IV) oxide 、 氯仿 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 6.0h， 以100%的产率得到tert-butyl (4S)-4-[(2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-1,3-oxazolidine-3-carboxylate;hydrochloride
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine

  摘要：

  The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylgiycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers was converted to the natural product and the other to its C-4 epimer. The C-4 configuration was established from NOESY NMR analysis and X-ray structure of compounds derived from the non-natural diastereoisomer. Thus, tetrallydrolathyrine was shown to have the (2S,4R) absolute configuration.

  DOI：

  10.1021/jo900800x
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 tert-butyl (4S)-4-[(2R)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,3-oxazolidine-3-carboxylate 、 tert-butyl (4S)-4-[(2S)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine

  摘要：

  The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylgiycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers was converted to the natural product and the other to its C-4 epimer. The C-4 configuration was established from NOESY NMR analysis and X-ray structure of compounds derived from the non-natural diastereoisomer. Thus, tetrallydrolathyrine was shown to have the (2S,4R) absolute configuration.

  DOI：

  10.1021/jo900800x