N-(2,3,6,2',3',4',6'-hepta-O-benzyl-β-D-maltosyl)-2,4-dinitrobenzenesulfonamide | 1385026-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,3,6,2',3',4',6'-hepta-O-benzyl-β-D-maltosyl)-2,4-dinitrobenzenesulfonamide
• CAS: 1385026-79-8
• 化学式: C₆₇H₅₃N₃O₂₃S
• 分子量: 1300.23
• InChiKey: JXDZQSFLGFTOEC-HSZLXKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  94.0
• 可旋转键数：
  23.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  344.24
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  N-(2,3,6,2',3',4',6'-hepta-O-benzyl-β-D-maltosyl)-2,4-dinitrobenzenesulfonamide 、 硫代乙酸 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以67%的产率得到N-(2,3,6,2',3',4',6'-hepta-O-benzoyl-β-D-maltosyl)acetamide
  参考文献：
  名称：

  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

  摘要：

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

  DOI：

  10.1080/07328303.2012.663431
• 作为产物：
  描述：

  2,4-二硝基苯磺酰氯 、 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.5h， 以43%的产率得到N-(2,3,6,2',3',4',6'-hepta-O-benzyl-β-D-maltosyl)-2,4-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

  摘要：

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

  DOI：

  10.1080/07328303.2012.663431