[1-(β-D-gluco-hept-2-ulopyranosyl)-4-phenyl-1,2,3-triazole]onamide | 1219686-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-(β-D-gluco-hept-2-ulopyranosyl)-4-phenyl-1,2,3-triazole]onamide
• 英文别名: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-(4-phenyltriazol-1-yl)oxane-2-carboxamide
• CAS: 1219686-57-3
• 化学式: C₁₅H₁₈N₄O₆
• 分子量: 350.331
• InChiKey: PUKXDDXZVNIBPJ-VVSAWPALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-phenyl-1,2,3-triazole]onamide 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到[1-(β-D-gluco-hept-2-ulopyranosyl)-4-phenyl-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

文献信息

• Synthesis of 1-(d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors
  作者：Éva Bokor、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2009.12.043

  日期：2010.2

  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.