(2S,3S,4S,1'S)-1-acetyl-3,4-dihydroxy-2-(1'-hydroxy-2'-(p-methoxybenzyloxy)ethyl)pyrrolidine | 678142-28-4

• 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,3S,4S,1'S)-1-acetyl-3,4-dihydroxy-2-(1'-hydroxy-2'-(p-methoxybenzyloxy)ethyl)pyrrolidine
• 英文别名: 1-[(2S,3S,4S)-3,4-dihydroxy-2-[(1S)-1-hydroxy-2-[(4-methoxyphenyl)methoxy]ethyl]pyrrolidin-1-yl]ethanone
• CAS: 678142-28-4
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: ONDNSHRYCWXFEN-XUWVNRHRSA-N

物化性质

• 沸点：
  550.1±50.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,1'S)-1-acetyl-3,4-dihydroxy-2-(1'-hydroxy-2'-(p-methoxybenzyloxy)ethyl)pyrrolidine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003
• 作为产物：
  描述：

  [(3S,4S,5S)-1-acetyl-4-benzoyloxy-5-[(1S)-1-hydroxy-2-[(4-methoxyphenyl)methoxy]ethyl]pyrrolidin-3-yl] benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到(2S,3S,4S,1'S)-1-acetyl-3,4-dihydroxy-2-(1'-hydroxy-2'-(p-methoxybenzyloxy)ethyl)pyrrolidine
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003