(3aS,4S,6S,6aR)-2,2,6-trimethyl-4-(4-methylphenyl)-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole | 1301240-47-0

• 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: (3aS,4S,6S,6aR)-2,2,6-trimethyl-4-(4-methylphenyl)-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 1301240-47-0
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: LCKMFDOLEXEOOD-DEQVHRJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6S,6aR)-2,2,6-trimethyl-4-(4-methylphenyl)-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 在 盐酸 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以73%的产率得到(2S,3S,4R,5S)-2-(p-tolyl)-5-methylpyrrolidine-3,4-diol
  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
• 作为产物：
  描述：

  5-deoxy-2,3-O-isopropylidene-D-ribofuranose 在 吡啶 、 palladium on carbon 、 氢气 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 95.0h， 生成 (3aS,4S,6S,6aR)-2,2,6-trimethyl-4-(4-methylphenyl)-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
  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.