4-acetoxymethyl-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-1,2,3-triazole | 1361485-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetoxymethyl-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-1,2,3-triazole
• 英文别名: 1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-acetoxymethyl-1,2,3-triazole；[1-[(2R,3R,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]triazol-4-yl]methyl acetate
• CAS: 1361485-88-2
• 化学式: C₁₆H₂₁N₃O₉
• 分子量: 399.357
• InChiKey: PFWIDPSFOWORKR-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-acetoxymethyl-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-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82%的产率得到1-(β-D-xylopyranosyl)-4-hydroxymethyl-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 18.0h， 生成 4-acetoxymethyl-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-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

• 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.