N-(2-deoxy-2-iodo-3,4,6-tri-O-methyl-α-D-mannopyranosyl)succinimide | 1316849-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-deoxy-2-iodo-3,4,6-tri-O-methyl-α-D-mannopyranosyl)succinimide
• CAS: 1316849-01-0
• 化学式: C₁₃H₂₀INO₆
• 分子量: 413.209
• InChiKey: IHJVRTWSUYKLBJ-UYYQOPGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(2-deoxy-2-iodo-3,4,6-tri-O-methyl-α-D-mannopyranosyl)succinimide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以91%的产率得到N-(2-deoxy-3,4,6-tri-O-methyl-α-D-arabinohexopyranosyl)succinimide
  参考文献：
  名称：

  En route to sugar–alkaloid conjugates

  摘要：

  After stereoselective addition of N-iodosuccinimide to glycals subsequent dehalogenation results in formation of N-glycopyranosyl succinimides. By UV irradiation both azepindiones and preferentially [5.3.1.0(2,6)] tricyclic oxalactams could be obtained. Their transformation into a number of novel sugar conjugates resembling some prominent alkaloid N-pyrrol components by thiation and reduction is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.022
• 作为产物：
  描述：

  N-碘代丁二酰亚胺 、 3,4,6-三-O-甲基-D-葡萄糖醛 以 乙腈 为溶剂， 反应 12.0h， 以89%的产率得到N-(2-deoxy-2-iodo-3,4,6-tri-O-methyl-α-D-mannopyranosyl)succinimide
  参考文献：
  名称：

  En route to sugar–alkaloid conjugates

  摘要：

  After stereoselective addition of N-iodosuccinimide to glycals subsequent dehalogenation results in formation of N-glycopyranosyl succinimides. By UV irradiation both azepindiones and preferentially [5.3.1.0(2,6)] tricyclic oxalactams could be obtained. Their transformation into a number of novel sugar conjugates resembling some prominent alkaloid N-pyrrol components by thiation and reduction is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.022