5,5'-(Methylenedi-4,1-phenylene)bis-2-methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole | 146815-18-1

• 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: 5,5'-(Methylenedi-4,1-phenylene)bis-2-methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole
• 英文别名: 3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-[4-[[4-[3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methyl-4,6-dioxo-3a,6a-dihydro-3H-pyrrolo[3,4-d][1,2]oxazol-5-yl]phenyl]methyl]phenyl]-2-methyl-3a,6a-dihydro-3H-pyrrolo[3,4-d][1,2]oxazole-4,6-dione
• CAS: 146815-18-1
• 化学式: C₃₉H₄₄N₄O₁₄
• 分子量: 792.797
• InChiKey: DPBWDXQZJXVFIH-XLKUZNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  57.0
• 可旋转键数：
  6.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  195.54
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime) 、 双马来酰亚胺 以 甲苯 为溶剂， 反应 1.0h， 以76%的产率得到5,5'-(Methylenedi-4,1-phenylene)bis-2-methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-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