methyl 4-O-crotonyl-6-deoxy-6-(2-iodobenzoylamino)-2,3-di-O-methyl-α-D-glucopyranoside | 793692-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-crotonyl-6-deoxy-6-(2-iodobenzoylamino)-2,3-di-O-methyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-2-[[(2-iodobenzoyl)amino]methyl]-4,5,6-trimethoxyoxan-3-yl] (E)-but-2-enoate
• CAS: 793692-20-3
• 化学式: C₂₀H₂₆INO₇
• 分子量: 519.333
• InChiKey: DCFFSGWGOZBTHM-BYPLEGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-O-crotonyl-6-deoxy-6-(2-iodobenzoylamino)-2,3-di-O-methyl-α-D-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以72%的产率得到[(2R,3R,4S,5R,6S)-2-(benzamidomethyl)-4,5,6-trimethoxyoxan-3-yl] (E)-but-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：

  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 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 methyl 4-O-crotonyl-6-deoxy-6-(2-iodobenzoylamino)-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