[1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-(2-naphthyl)-1,2,3-triazole]onamide | 1219686-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-(2-naphthyl)-1,2,3-triazole]onamide
• CAS: 1219686-54-0
• 化学式: C₄₇H₃₆N₄O₁₀
• 分子量: 816.824
• InChiKey: NCNREFYTYJPZAO-YZDLDTKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  61.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  188.23
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-(2-naphthyl)-1,2,3-triazole]onamide 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以81%的产率得到[1-(β-D-gluco-hept-2-ulopyranosyl)-4-(2-naphthyl)-1,2,3-triazole]onamide
  参考文献：
  名称：

  Synthesis of 1-(d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors

  摘要：

  1-(D-Glucopyranosyl)-1,2,3-triazoles were prepared from per-O-acetylated alpha-and beta-D-glucopyranosyl azides as well as per-O-benzoylated (beta-D-gluco-hept-2-ulopyranosylazide)onamide and onic acid methylester by using azide-alkyne cycloaddition catalysed by in situ generated Cu(I) under aqueous conditions. The O-acyl protecting groups were removed by the Zemplen protocol. The test compounds were assayed against rabbit muscle glycogen phosphorylase b to show that the b-D-glucopyranosyl derivatives were superior inhibitors as compared to the two other series of triazoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.043
• 作为产物：
  描述：

  C-(1-azido-2,3,4,6-tetra-O-benzoyl-1-deoxy-α-D-glucopyranosyl)formamide 、 2-乙基萘 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以87%的产率得到[1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-(2-naphthyl)-1,2,3-triazole]onamide
  参考文献：
  名称：

  Synthesis of 1-(d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors

  摘要：

  1-(D-Glucopyranosyl)-1,2,3-triazoles were prepared from per-O-acetylated alpha-and beta-D-glucopyranosyl azides as well as per-O-benzoylated (beta-D-gluco-hept-2-ulopyranosylazide)onamide and onic acid methylester by using azide-alkyne cycloaddition catalysed by in situ generated Cu(I) under aqueous conditions. The O-acyl protecting groups were removed by the Zemplen protocol. The test compounds were assayed against rabbit muscle glycogen phosphorylase b to show that the b-D-glucopyranosyl derivatives were superior inhibitors as compared to the two other series of triazoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.043