N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide | 1196872-34-0

• 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-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2,4-dinitrophenyl)sulfonylamino]oxan-2-yl]methyl acetate
• CAS: 1196872-34-0
• 化学式: C₂₀H₂₄N₄O₁₄S
• 分子量: 576.495
• InChiKey: YXBNBCFZEICOLN-YHUYVZNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  263
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Boc-L-Asp(α-OBn)-γ-SH 、 N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以69%的产率得到2-acetamido-3,4,6-tri-O-acetyl-1-N-<1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl>-2-deoxy-D-glucopyranosylamine
  参考文献：
  名称：

  Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids

  摘要：

  N-Glucosyl-2,4-dinitrobenzenesulfonamide was prepared from N-acetyl-D-glucosamine and 2,4-dinitrobenzenesulfonyl chloride. Amidation of several thioacids using the N-glucosylsulfonamide donor proceeded smoothly to give the desired N-glucosylamides in good to high yields. The amidation reactions were carried out at room temperature, under mild conditions, and were completed in a very short time. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.002
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-3,4,6-三-邻乙酰基-beta-d-吡喃葡萄糖胺 、 2,4-二硝基苯磺酰氯 在 吡啶 作用下， 反应 3.0h， 以0.078 g的产率得到N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids

  摘要：

  N-Glucosyl-2,4-dinitrobenzenesulfonamide was prepared from N-acetyl-D-glucosamine and 2,4-dinitrobenzenesulfonyl chloride. Amidation of several thioacids using the N-glucosylsulfonamide donor proceeded smoothly to give the desired N-glucosylamides in good to high yields. The amidation reactions were carried out at room temperature, under mild conditions, and were completed in a very short time. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.002