N-(((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)acetamide | 1105054-56-5

• 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: N-(((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)acetamide
• 英文别名: N-[[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]acetamide
• CAS: 1105054-56-5
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: UQEQPFWCYJXMDK-XAMCCFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5S)-2-(aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol 、 乙酸酐 反应 0.17h， 以92%的产率得到N-(((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)acetamide
  参考文献：
  名称：

  A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

  摘要：

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.096

文献信息

• A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP
  作者：En-Lun Tsou、Yao-Ting Yeh、Pi-Hui Liang、Wei-Chieh Cheng

  DOI：10.1016/j.tet.2008.10.096

  日期：2009.1

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.