1-(6'-deoxy-1',2':3',4'-di-O-isopropylidene-α-D-glucopyranos-6'-yl)-1H-pyrrole-2,5-dione | 1416951-66-0

• 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: 1-(6'-deoxy-1',2':3',4'-di-O-isopropylidene-α-D-glucopyranos-6'-yl)-1H-pyrrole-2,5-dione
• CAS: 1416951-66-0
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: JRMRDJAPJJONRZ-AEOCFKNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(6'-deoxy-1',2':3',4'-di-O-isopropylidene-α-D-glucopyranos-6'-yl)-1H-pyrrole-2,5-dione 、 benzohydroximoyl chloride 在 三乙胺 、 magnesium bromide 作用下， 以 甲苯 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines

  摘要：

  Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64-20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76-84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,45,5S,6S,3aR,6a5)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.005
• 作为产物：
  描述：

  6-amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 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 3.0h， 生成 1-(6'-deoxy-1',2':3',4'-di-O-isopropylidene-α-D-glucopyranos-6'-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines

  摘要：

  Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64-20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76-84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,45,5S,6S,3aR,6a5)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.005