ethyl 1-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,3-triazole-4-carboxylate | 1219686-45-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,3-triazole-4-carboxylate
• 英文别名: ethyl 1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazole-4-carboxylate
• CAS: 1219686-45-9
• 化学式: C₁₉H₂₅N₃O₁₁
• 分子量: 471.421
• InChiKey: DTLAJOWEGSUGTP-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,3-triazole-4-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以47%的产率得到sodium 1-(α-D-glucopyranosyl)-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：

  丙炔酸乙酯 、 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 在 bis-triphenylphosphano-copper(I)-butyrate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到ethyl 1-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles

  摘要：

  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.

  DOI：

  10.1016/j.carres.2012.01.004