(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-5-(benzoyloxymethyl)-1-N-benzyl-3,4-O-isopropylidenepyrrolidine-3,4-diol | 1155986-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-5-(benzoyloxymethyl)-1-N-benzyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
• 英文别名: [(3aS,4R,6S,6aR)-4-(1-aminocyclopropyl)-5-benzyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methyl benzoate
• CAS: 1155986-12-1
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: DKBANNUDQAIMQT-CBPXPLCBSA-N

物化性质

• 沸点：
  524.8±50.0 °C(predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  benzylammonium formate 在 吡啶 、 titanium(IV) isopropylate 、 METHYLTITANIUM TRIISOPROPOXIDE 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 28.0h， 生成 (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-N-benzyl-5-(hydroxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol 、 (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-5-(benzoyloxymethyl)-1-N-benzyl-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。