(2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol | 1357516-70-1

• 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)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol
• CAS: 1357516-70-1
• 化学式: C₃₄H₃₄N₃O₂P
• 分子量: 547.637
• InChiKey: QAEMFYSPMSGXMO-JDIHBLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol 在 甲醇 、 氨 作用下， 以99%的产率得到(2R,3S,4R,5S)-5-(aminomethyl)-1-benzyl-2-cyano-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：

  (2R,3S,4R,5S)-5-azidomethyl-1-N-benzyl-2-cyano-3,4-dihydroxy-3,4-O-isopropylidenepyrrolidine 、 三苯基膦 在 magnesium bromide ethyl etherate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 以88%的产率得到(2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-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