tert-butyl (4S)-4-[(2R)-4-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-1,3-oxazolidine-3-carboxylate | 1174408-12-8

• 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)-4-[(2R)-4-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 1174408-12-8
• 化学式: C₃₄H₄₅N₅O₁₀
• 分子量: 683.759
• InChiKey: YDWUTKUPFZYMJU-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  183
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(2R)-4-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-1,3-oxazolidine-3-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78%的产率得到benzyl N-[(4R)-4-[[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl]-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：

  tert-butyl (4S)-4-[(2R)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-1,3-oxazolidine-3-carboxylate;hydrochloride 、 1,3-二(苄氧羰基)-2-甲基异硫脲 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl (4S)-4-[(2R)-4-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-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

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.