4-epi-(+)-codonopsinine | 1301240-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-epi-(+)-codonopsinine
• 英文别名: (2s,3s,4r,5s)-2-(4-Methoxyphenyl)-1,5-Dimethylpyrrolidine-3,4-Diol
• CAS: 1301240-35-6
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: GJZNAEFHIYPPEM-KNDHEWATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以75%的产率得到4-epi-(+)-codonopsinine
  参考文献：
  名称：

  Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

  摘要：

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.

  DOI：

  10.1021/jo200176u

文献信息

• Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-<i>epi</i>-(+)-Codonopsinine
  作者：Alexis Kotland、Fabien Accadbled、Koen Robeyns、Jean-Bernard Behr

  DOI：10.1021/jo200176u

  日期：2011.5.20

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.