tert-butyl (3S,5S)-5-[2-[[amino-(methoxycarbonylamino)methylidene]amino]ethyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopyrrolidine-1-carboxylate | 1174408-18-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3S,5S)-5-[2-[[amino-(methoxycarbonylamino)methylidene]amino]ethyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopyrrolidine-1-carboxylate
• CAS: 1174408-18-4
• 化学式: C₁₉H₃₃N₅O₇
• 分子量: 443.5
• InChiKey: LXELXCAGVPJURD-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 3.0h， 以12%的产率得到tert-butyl (3S,5S)-5-[2-[[amino-(methoxycarbonylamino)methylidene]amino]ethyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopyrrolidine-1-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.