N-ethyl-2-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-succinimide | 116454-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-ethyl-2-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-succinimide
• CAS: 116454-27-4
• 化学式: C₂₀H₂₇NO₁₁
• 分子量: 457.434
• InChiKey: BNWZZRKRXRPBNF-BERMTMLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  151.81
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N-乙基马来酰亚胺 、 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 在 三正丁基氢锡 作用下， 以 苯 为溶剂， 以55%的产率得到N-ethyl-2-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-succinimide
  参考文献：
  名称：

  Glycosyl iodides. History and recent advances

  摘要：

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.032

文献信息

• Synthesis of -glycosyl compounds by the addition of glycosyl radicals to olefins
  作者：Younosuke Araki、Tadatoshi Endo、Masaki Tanji、Jun'ichi Nagasawa、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(01)81072-8

  日期：1987.1

  The Bu3SnH - AIBN induced radical additions of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl derivatives, bearing α-Br (1), α-I (5) β-OCSSMe (7), and β-SePh (8) groups on the anomeric carbon, with olefins such as dimethyl maleate, methyl vinyl ketone, dimethyl acetylenedicarboxylate, butyl vinyl ether, and -ethylmaleimide were examined for a synthesis of -glycosyl compounds.

  Bu 3 SnH-AIBN诱导的带有α-Br（1），α-I（5）β-OCSSMe（7）的2,3,4,6-四-O-乙酰基-D-吡喃葡萄糖基衍生物的自由基加成，检查了异头碳上的β-SePh（8）基团和烯烃，例如马来酸二甲酯，甲基乙烯基酮，乙炔二羧酸二甲酯，丁基乙烯基醚和-乙基马来酰亚胺，以合成-糖基化合物。