methyl 6-azido-4-O-cinnamoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside | 793692-18-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 6-azido-4-O-cinnamoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
• CAS: 793692-18-9
• 化学式: C₁₈H₂₃N₃O₆
• 分子量: 377.397
• InChiKey: MGHBQBNZZGASQE-GQYVTKONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.98
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-4-O-cinnamoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 、 三苯基膦 作用下， 以 乙醚 、 苯 为溶剂， 反应 6.0h， 生成 [(2R,3R,4S,5R,6S)-4,5,6-trimethoxy-2-[(propanoylamino)methyl]oxan-3-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Synthesis of unexpected six-membered imides by free-radical carbocyclisation on carbohydrate templates

  摘要：

  Free-radical reactions of amido-esters anchored to a carbohydrate derived from methyl alpha-D-glucopyranoside afforded unexpected six-membered cyclic imides. Their structures were elucidated by ESI-MS/MS and NMR spectral analyses, and a mechanism for the formation of these imides is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.039
• 作为产物：
  描述：

  肉桂酸 、 methyl 6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 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 12.0h， 以85%的产率得到methyl 6-azido-4-O-cinnamoyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of unexpected six-membered imides by free-radical carbocyclisation on carbohydrate templates

  摘要：

  Free-radical reactions of amido-esters anchored to a carbohydrate derived from methyl alpha-D-glucopyranoside afforded unexpected six-membered cyclic imides. Their structures were elucidated by ESI-MS/MS and NMR spectral analyses, and a mechanism for the formation of these imides is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.039