N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide | 1385026-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,4-dinitrobenzenesulfonamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2,4-dinitrophenyl)sulfonylamino]oxan-2-yl]methyl benzoate
• CAS: 1385026-75-4
• 化学式: C₄₀H₃₁N₃O₁₅S
• 分子量: 825.763
• InChiKey: QSMBBZJEGPGOEP-HNVKGOKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  261
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-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68%的产率得到(2R,3R,4S,5R,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  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：

  D-glucopyranosyl azide 在 吡啶 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-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

文献信息

• Synthesis of β-Glycosyl Amides from <i>N</i>-Glycosyl Dinitrobenzenesulfonamides
  作者：Vishwanath Gaitonde、Steven J. Sucheck

  DOI：10.1080/07328303.2012.663431

  日期：2012.5.1

  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.