4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole | 34280-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole
• 英文别名: 4-phenyl-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-1,2,3-triazole；1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-phenyl-1,2,3-triazole；tri-O-acetyl-1-(4-phenyl-[1,2,3]triazol-1-yl)-β-D-1-deoxy-xylopyranose；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-(4-phenyltriazol-1-yl)oxan-3-yl] acetate
• CAS: 34280-00-7
• 化学式: C₁₉H₂₁N₃O₇
• 分子量: 403.392
• InChiKey: CXRJFHDWYSOZQE-FCGDIQPGSA-N

物化性质

• 熔点：
  248 °C (sublm)
• 沸点：
  538.3±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole 在 甲醇 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以99%的产率得到1-(β-D-xylopyranosyl)-4-phenyl-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of 1,2,3-triazoles from xylosyl and 5-thioxylosyl azides: evaluation of the xylose scaffold for the design of potential glycogen phosphorylase inhibitors

  摘要：

  Various acetylenic derivatives and acetylated beta-D-xylopyranosyl azide or the 5-thio-beta-D-xylopyranosyl analogue were coupled by Cu(I)-catalyzed azide alkyne 1,3-dipolar cycloaddition (CuAAC) to afford a series of 1-xylosyl-4-substituted 1,2,3-triazoles. Controlled oxidation of the endocyclic sulfur atom of the 5-thioxylose moiety led to the corresponding sulfoxides and sulfones. Deacetylation afforded 19 hydroxylated xylose and 5-thioxylose derivatives, found to be only sparingly water-soluble. Compared to glucose-based analogues, they appeared to be much weaker inhibitors of glycogen phosphorylase, as the absence of a hydroxymethyl group weakens their binding at the enzyme active site. However, such new xylose derivatives might be useful glycomimetics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.09.020
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 copper(l) iodide 、 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole
  参考文献：
  名称：

  Synthesis of 1,2,3-triazoles from xylosyl and 5-thioxylosyl azides: evaluation of the xylose scaffold for the design of potential glycogen phosphorylase inhibitors

  摘要：

  Various acetylenic derivatives and acetylated beta-D-xylopyranosyl azide or the 5-thio-beta-D-xylopyranosyl analogue were coupled by Cu(I)-catalyzed azide alkyne 1,3-dipolar cycloaddition (CuAAC) to afford a series of 1-xylosyl-4-substituted 1,2,3-triazoles. Controlled oxidation of the endocyclic sulfur atom of the 5-thioxylose moiety led to the corresponding sulfoxides and sulfones. Deacetylation afforded 19 hydroxylated xylose and 5-thioxylose derivatives, found to be only sparingly water-soluble. Compared to glucose-based analogues, they appeared to be much weaker inhibitors of glycogen phosphorylase, as the absence of a hydroxymethyl group weakens their binding at the enzyme active site. However, such new xylose derivatives might be useful glycomimetics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.09.020

文献信息

• Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles: Copper-Catalyzed Cycloaddition of Organic Azides and Mixed Aluminum Acetylides
  作者：Yuhan Zhou、Thomas Lecourt、Laurent Micouin

  DOI：10.1002/anie.200907016

  日期：2010.3.29

  Al together now: Aluminotriazoles are obtained in a fully chemo‐ and regioselective manner by a copper‐catalyzed cycloaddition of organic azides with mixed‐aluminum acetylides (see scheme). The carbonaluminum bond, which is unaffected by the first transformation, is still able to react further with different electrophiles.

  现在在一起的是Al：铝三唑是通过有机叠氮化物与混合铝乙炔化物的铜催化环加成反应而以完全化学和区域选择性方式获得的（请参见方案）。不受第一个转化影响的碳铝键仍然能够与不同的亲电试剂进一步反应。
• 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.