benzyl N-[(6S)-6-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1,4,5,6-tetrahydropyrimidin-2-yl]carbamate | 1174408-15-1

• 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: benzyl N-[(6S)-6-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1,4,5,6-tetrahydropyrimidin-2-yl]carbamate
• CAS: 1174408-15-1
• 化学式: C₂₀H₃₀N₄O₅
• 分子量: 406.482
• InChiKey: QTPAMRYPERLJTO-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(6S)-6-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1,4,5,6-tetrahydropyrimidin-2-yl]carbamate 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90%的产率得到(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(6S)-2-(phenylmethoxycarbonylamino)-1,4,5,6-tetrahydropyrimidin-6-yl]propanoic acid
  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)-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

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.