C-(1,2-O-Isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-N-phenylnitrone | 146814-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(1,2-O-Isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-N-phenylnitrone
• 英文别名: 1-[(3aR,5R,6S,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-N-phenylmethanimine oxide
• CAS: 146814-99-5
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: OVIAAIKTFLIZGE-ZAZQJCJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(2,6-二甲基苯基)-1H-吡咯-2,5-二酮 、 C-(1,2-O-Isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-N-phenylnitrone 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides

  摘要：

  The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10. The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2. The structure and steric configuration of the products have been assigned on the basis of H-1 and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00810931
• 作为产物：
  描述：

  苯基羟胺 、 3-O-acetyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 以83%的产率得到C-(1,2-O-Isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-N-phenylnitrone
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides

  摘要：

  The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10. The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2. The structure and steric configuration of the products have been assigned on the basis of H-1 and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00810931