5-thio-β-D-xylopyranosyl-4-hydroxymethyl-1,2,3-triazole | 1415685-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-thio-β-D-xylopyranosyl-4-hydroxymethyl-1,2,3-triazole
• 英文别名: (2R,3R,4S,5S)-2-[4-(hydroxymethyl)triazol-1-yl]thiane-3,4,5-triol
• CAS: 1415685-54-9
• 化学式: C₈H₁₃N₃O₄S
• 分子量: 247.275
• InChiKey: AHEHLJLQZVKZAW-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide 在 甲醇 、 copper(l) iodide 、 sodium azide 、 sodium methylate 、 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 4.0h， 生成 5-thio-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

文献信息

• 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
  作者：David Goyard、Marc Baron、Paraskevi V. Skourti、Aikaterini S. Chajistamatiou、Tibor Docsa、Pál Gergely、Evangelia D. Chrysina、Jean-Pierre Praly、Sébastien Vidal

  DOI：10.1016/j.carres.2012.09.020

  日期：2012.12

  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.