1'-(4-(1-hydroxyhexyl)-[1,2,3]-triazol-1-yl)-2',3',5'-tri-O-acetyl-β-D-ribofuranose | 1386989-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-(4-(1-hydroxyhexyl)-[1,2,3]-triazol-1-yl)-2',3',5'-tri-O-acetyl-β-D-ribofuranose
• CAS: 1386989-00-9
• 化学式: C₁₉H₂₉N₃O₈
• 分子量: 427.455
• InChiKey: DNTRSIMUYGBRBP-CXOVQGTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  139.07
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  beta-D-呋喃核糖 在 iron(III) chloride 、 copper(l) iodide 、 叠氮基三甲基硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.58h， 生成 1'-(4-(1-hydroxyhexyl)-[1,2,3]-triazol-1-yl)-2',3',5'-tri-O-acetyl-β-D-ribofuranose
  参考文献：
  名称：

  Ultrasound-assisted one-pot synthesis of anti-CML nucleosides featuring 1,2,3-triazole nucleobase under iron-copper catalysis

  摘要：

  A simple and efficient synthesis of modified 1,2,3-triazole nucleosides was developed. The strategy involved sequential one-pot acetylation-azidation-cycloaddition procedure and was found to be highly effective under a cooperative effect of ultrasound activation and iron/copper catalysis. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions. This one-pot procedure provides several advantages such as operational simplicity, high yield, safety and environment friendly protocol. The resulting substituted nucleosides were evaluated for their anticancer activity against K562 chronic myelogenous leukemia (CML) cell line Crown Copyright (C) 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.04.007