[1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-1,2,3-triazole]onamide | 1219686-52-8

• 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-ethoxycarbonyl-1,2,3-triazole]onamide
• 英文别名: [4-ethoxycarbonyl-1-(3',4',5',7'-tetra-O-benzoyl-β-D-glucohept-2-ulopyranosyl)-1,2,3-triazole]onamide；ethyl 1-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)-2-carbamoyloxan-2-yl]triazole-4-carboxylate
• CAS: 1219686-52-8
• 化学式: C₄₀H₃₄N₄O₁₂
• 分子量: 762.73
• InChiKey: BHSDRSAEPPINOU-GWZBVCSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  14

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-ethoxycarbonyl-1,2,3-triazole]onamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以67%的产率得到sodium [1-(β-D-gluco-hept-2-ulopyranosyl)onamide]-1,2,3-triazole-4-carboxylate
  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 、 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56%的产率得到[1-(3',4',5',7'-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)-4-ethoxycarbonyl-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

• Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles
  作者：Éva Bokor、Csenge Koppány、Zsombor Gonda、Zoltán Novák、László Somsák

  DOI：10.1016/j.carres.2012.01.004

  日期：2012.4

  Bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) was applied for the synthesis of O-peracylated 1-glycopyranosyl-4-substituted-1,2,3-triazoles from the corresponding glycosyl azides and alkynes. This catalyst proved superior to the CuSO4/L-ascorbic acid system even with sterically hindered and less reactive glycosyl azides. (C) 2012 Elsevier Ltd. All rights reserved.