(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-N-benzyl-5-(hydroxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol | 1155986-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-N-benzyl-5-(hydroxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol
• CAS: 1155986-15-4
• 化学式: C₁₈H₂₆N₂O₃
• 分子量: 318.416
• InChiKey: QTMOVFVFFDALKA-JJXSEGSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-5-(benzoyloxymethyl)-1-N-benzyl-3,4-O-isopropylidenepyrrolidine-3,4-diol 在 甲醇 、 氨 作用下， 以68%的产率得到(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-N-benzyl-5-(hydroxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions

  摘要：

  The titanium-mediated cyclopropanation reaction using Ti((OPr)-Pr-i)(3)Me/EtMgBr/BF3 center dot OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as L-fucose, is a moderate (IC50=44 mu M), but selective, inhibitor of alpha-L-fucosidase from human placenta. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.024

文献信息

• Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles
  作者：Delphine Declerck、Solen Josse、Albert Nguyen Van Nhien、Denis Postel

  DOI：10.1016/j.tetlet.2009.02.135

  日期：2009.5

  We have developed an expedient method for the synthesis of 2-aminocyclopropyl pyrrolidines from carbohydrate-derived α-aminonitriles involving up to five or six steps, the key step being the titanium-mediated aminocyclopropanation on the aminonitrile moiety, followed by cleavage of the protecting groups.

  我们已经开发了一种从碳水化合物衍生的α-氨基腈合成2个氨基环丙基吡咯烷的简便方法，涉及多达五或六个步骤，关键步骤是在氨基腈部分进行钛介导的氨基环丙烷化，然后裂解保护基。