6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11S)-11-azido-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate | 1155262-97-7

• 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: 6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11S)-11-azido-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate
• CAS: 1155262-97-7
• 化学式: C₁₇H₂₃N₅O₆
• 分子量: 393.4
• InChiKey: DUUQRQXHVSMOJN-HTFCKZLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11S)-11-azido-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11S)-11-amino-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of Proline-Based Diketopiperazine Scaffolds

  摘要：

  A number of natural products with interesting biological properties are based on a diketopiperazine scaffold. In this context, we have developed a diversity oriented and efficient synthetic strategy to highly functionalized proline-based diketopiperazines. In this paper we describe the stereoselective synthesis of various scaffolds resembling abundant natural product core structures. These scaffolds can be conjugated to a solid phase and are thus platforms for the construction of small compound libraries and the synthesis of natural products with diketopiperazine cores.

  DOI：

  10.1021/jo9004876
• 作为产物：
  描述：

  6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11R)-11-(4-methylphenyl)sulfonyloxy-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11S)-11-azido-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of Proline-Based Diketopiperazine Scaffolds

  摘要：

  A number of natural products with interesting biological properties are based on a diketopiperazine scaffold. In this context, we have developed a diversity oriented and efficient synthetic strategy to highly functionalized proline-based diketopiperazines. In this paper we describe the stereoselective synthesis of various scaffolds resembling abundant natural product core structures. These scaffolds can be conjugated to a solid phase and are thus platforms for the construction of small compound libraries and the synthesis of natural products with diketopiperazine cores.

  DOI：

  10.1021/jo9004876