(Z)-4-oxo-4-(((3S,4S,5R,6R)-1,2,3,4-di-O-isopropylidenetetrahydro-2H-pyran-2-yl)methylamino)but-2-enoic acid | 1416951-65-9

• 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: (Z)-4-oxo-4-(((3S,4S,5R,6R)-1,2,3,4-di-O-isopropylidenetetrahydro-2H-pyran-2-yl)methylamino)but-2-enoic acid
• CAS: 1416951-65-9
• 化学式: C₁₆H₂₃NO₈
• 分子量: 357.361
• InChiKey: HHNZDOMMXHEUFQ-VKKPZTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-oxo-4-(((3S,4S,5R,6R)-1,2,3,4-di-O-isopropylidenetetrahydro-2H-pyran-2-yl)methylamino)but-2-enoic acid 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， 以70%的产率得到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
• 作为产物：
  描述：

  (3AR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-5-(tosylmethyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran 在 sodium azide 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (Z)-4-oxo-4-(((3S,4S,5R,6R)-1,2,3,4-di-O-isopropylidenetetrahydro-2H-pyran-2-yl)methylamino)but-2-enoic acid
  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