tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S,4R)-4-(4-methylphenyl)sulfonyloxy-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate | 1155262-90-0

• 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 (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S,4R)-4-(4-methylphenyl)sulfonyloxy-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 1155262-90-0
• 化学式: C₃₁H₃₈N₂O₁₀S
• 分子量: 630.716
• InChiKey: GOYCIEQCNGPQCO-ZYUYTQNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S,4R)-4-(4-methylphenyl)sulfonyloxy-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate 在 ruthenium(III) chloride trihydrate 、 高碘酸 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成
  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：

  、 (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester 以 N,N-二甲基甲酰胺 为溶剂， 以6.34 g的产率得到tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S,4R)-4-(4-methylphenyl)sulfonyloxy-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
  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