5-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose | 649571-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
• CAS: 649571-93-7
• 化学式: C₂₂H₂₉NO₇
• 分子量: 419.475
• InChiKey: HOAOFVLJZBTTLE-VHKDHRAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  86.69
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 5-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到5-[(3R,5S)-1-benzyl-3-[(1R)-1-methoxy-1-phenyl-1-(trifluoromethyl)acetoxy]-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027
• 作为产物：
  描述：

  (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 在 水 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 5-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027