methyl [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-1,2,3-triazole]onate | 1219686-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-1,2,3-triazole]onate
• CAS: 1219686-36-8
• 化学式: C₄₁H₃₅N₃O₁₃
• 分子量: 777.741
• InChiKey: KMEUQGIIWZLBKN-DWEOFCAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  57.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  197.74
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-1,2,3-triazole]onate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以35%的产率得到[1-(β-D-gluco-hept-2-ulopyranosyl)-4-carboxylato-1,2,3-triazole]onic acid disodium salt
  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：

  methyl 2-azido-3,4,5,7-tetra-O-benzoyl-2-deoxy-β-D-gluco-hept-2-ulopyranosonate 、 丙炔酸乙酯 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 水 为溶剂， 反应 8.0h， 以70%的产率得到methyl [1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-1,2,3-triazole]onate
  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