(2S,3S,4R,5S)-N-(4-methoxybenzyl)-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol | 1301240-41-4

• 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: (2S,3S,4R,5S)-N-(4-methoxybenzyl)-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol
• 英文别名: (3aS,4S,6S,6aR)-4-(4-methoxyphenyl)-5-[(4-methoxyphenyl)methyl]-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 1301240-41-4
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: UXIQSHYULMAMCJ-RWXMBLCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-N-(4-methoxybenzyl)-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以46%的产率得到(3aS,4S,6S,6aR)-4-(4-methoxyphenyl)-2,2,6-trimethyl-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
• 作为产物：
  描述：

  5-deoxy-2,3-O-isopropylidene-D-ribofuranose 在 吡啶 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 (2S,3S,4R,5S)-N-(4-methoxybenzyl)-2-[4-methoxyphenyl]-3,4-O-isopropylidene-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

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.