1-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-4-acetoxymethyl-1,2,3-triazole S,S-dioxide | 1415685-73-2

• 英文名称: 1-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-4-acetoxymethyl-1,2,3-triazole S,S-dioxide
• CAS: 1415685-73-2
• 化学式: C₁₆H₂₁N₃O₁₀S
• 分子量: 447.423
• InChiKey: IWESYRQYFRBLCF-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  170.05
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-4-acetoxymethyl-1,2,3-triazole S,S-dioxide 在 甲醇 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到1-(5-thio-β-D-xylopyranosyl)-4-hydroxymethyl-1,2,3-triazole S,S-dioxide
  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：

  1-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-4-(acetoxymethyl)-1,2,3-triazole 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 以99%的产率得到1-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-4-acetoxymethyl-1,2,3-triazole S,S-dioxide
  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