4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose | 649571-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
• CAS: 649571-87-9
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: AEPMFFHKUWOCQV-QQBNBFENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  84.92
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-[(3S,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose 在 4-二甲氨基吡啶 、 水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 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：

  丙烯酸甲酯（MA） 、 (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 反应 0.5h， 以74%的产率得到methyl (2R,3R,5R)-2-benzyl-3-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)isoxazolidine-5-carboxylate
  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