[(2S,3R,4S)-4-acetamido-3-acetyloxy-1-benzylpyrrolidin-2-yl]methyl acetate | 944329-23-1

• 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: [(2S,3R,4S)-4-acetamido-3-acetyloxy-1-benzylpyrrolidin-2-yl]methyl acetate
• CAS: 944329-23-1
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: WKYNQKYFVZDLTG-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S)-4-acetamido-3-acetyloxy-1-benzylpyrrolidin-2-yl]methyl acetate 在 钯 氢气 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 N-((3S,4R,5S)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl)acetamide
  参考文献：
  名称：

  Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases

  摘要：

  The synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideOXY-L-arabinitoI LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol DABNAc, was prepared from L-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors Of D-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while Dimino sugar mimics inhibit D-glycohydrolases competitively, their L-enantiomers show non-competitive inhibition and in the case of iminofuranoses L-enantiomers are usually more potent inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.041
• 作为产物：
  描述：

  (3R,4S,5R)-3,4-二羟基-5-(羟基甲基)二氢-2(3H)-呋喃酮 在 palladium on activated charcoal 吡啶 、 盐酸 、 锂硼氢 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(2S,3R,4S)-4-acetamido-3-acetyloxy-1-benzylpyrrolidin-2-yl]methyl acetate
  参考文献：
  名称：

  Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases

  摘要：

  The synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideOXY-L-arabinitoI LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol DABNAc, was prepared from L-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors Of D-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while Dimino sugar mimics inhibit D-glycohydrolases competitively, their L-enantiomers show non-competitive inhibition and in the case of iminofuranoses L-enantiomers are usually more potent inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.041