tert-butyl (4S)-2-oxo-4-[[(4S)-2-(phenylmethoxycarbonylamino)-1,4,5,6-tetrahydropyrimidin-4-yl]methyl]-1,3-oxazolidine-3-carboxylate | 1174408-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (4S)-2-oxo-4-[[(4S)-2-(phenylmethoxycarbonylamino)-1,4,5,6-tetrahydropyrimidin-4-yl]methyl]-1,3-oxazolidine-3-carboxylate
• CAS: 1174408-21-9
• 化学式: C₂₁H₂₈N₄O₆
• 分子量: 432.477
• InChiKey: AXNIBMAGLWINEJ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-2-oxo-4-[[(4S)-2-(phenylmethoxycarbonylamino)-1,4,5,6-tetrahydropyrimidin-4-yl]methyl]-1,3-oxazolidine-3-carboxylate 在 甲醇 、 caesium carbonate 作用下， 以70%的产率得到benzyl N-[(6S)-6-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1,4,5,6-tetrahydropyrimidin-2-yl]carbamate
  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 、 benzyl N-[(4S)-4-[[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl]-1,4,5,6-tetrahydropyrimidin-2-yl]carbamate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以73%的产率得到tert-butyl (4S)-2-oxo-4-[[(4S)-2-(phenylmethoxycarbonylamino)-1,4,5,6-tetrahydropyrimidin-4-yl]methyl]-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

文献信息

• Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine
  作者：Meryem Benohoud、Loïc Leman、Silvia H. Cardoso、Pascal Retailleau、Philippe Dauban、Josiane Thierry、Robert H. Dodd

  DOI：10.1021/jo900800x

  日期：2009.8.7

  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.