(1R)-N-hydroxy-N-(2',3':5',6'-O-diisopropylidene-α-D-mannofuranosyl)-α-2-propenylbenzenemethanamine | 133986-07-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-N-hydroxy-N-(2',3':5',6'-O-diisopropylidene-α-D-mannofuranosyl)-α-2-propenylbenzenemethanamine
• CAS: 133986-07-9；133986-08-0
• 化学式: C₂₂H₃₁NO₆
• 分子量: 405.491
• InChiKey: YAMRHODIWWJJLG-XUFBONQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R)-N-hydroxy-N-(2',3':5',6'-O-diisopropylidene-α-D-mannofuranosyl)-α-2-propenylbenzenemethanamine 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 生成 (3R,5S)-N-(2',3':5',6'-O-diisopropylidene-α-D-mannofuranosyl)-3-phenyl-5-(iodomethyl)isoxazolidine
  参考文献：
  名称：

  A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines

  摘要：

  N,N-Dialkyl-O-trialkylsilyl homoallylic hydroxylamines reacted with iodine, N-iodosuccinimide, or iodine chloride to give 3,5-disubstituted isoxazolidines in good yield. The relative configuration that was generated at C3 and C5 was controlled by the nature of the nitrogen substituent of the parent hydroxylamine: the presence of a primary alkyl group favored the formation of a cis-isoxazolidine, whereas the presence of a tert-butyl group favored the formation of a trans-isoxazolidine. The effects that the N- and O-substituents and the nature of the iodinating agent exerted on the stereoselectivity of the cyclization were examined. The synthesis of enantiomerically pure isoxazolidines from hydroxylamines carrying a chiral N-mannofuranosyl group is described.

  DOI：

  10.1021/jo00013a032
• 作为产物：
  描述：

  氯丙烯镁 、 2,3:5,6-di[-O-(1-methylethylidene)]-N-(phenylmethylene)-α-D-mannofuranosylamine N-oxide 以 四氢呋喃 为溶剂， 以36%的产率得到(1S)-N-hydroxy-N-(2',3':5',6'-O-diisopropylidene-α-D-mannofuranosyl)-α-2-propenylbenzenemethanamine
  参考文献：
  名称：

  A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines

  摘要：

  N,N-Dialkyl-O-trialkylsilyl homoallylic hydroxylamines reacted with iodine, N-iodosuccinimide, or iodine chloride to give 3,5-disubstituted isoxazolidines in good yield. The relative configuration that was generated at C3 and C5 was controlled by the nature of the nitrogen substituent of the parent hydroxylamine: the presence of a primary alkyl group favored the formation of a cis-isoxazolidine, whereas the presence of a tert-butyl group favored the formation of a trans-isoxazolidine. The effects that the N- and O-substituents and the nature of the iodinating agent exerted on the stereoselectivity of the cyclization were examined. The synthesis of enantiomerically pure isoxazolidines from hydroxylamines carrying a chiral N-mannofuranosyl group is described.

  DOI：

  10.1021/jo00013a032