1-[(1-pyrenyl)ethynyl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-β-D-ribofuranose | 1207741-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-[(1-pyrenyl)ethynyl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-β-D-ribofuranose
• 英文别名: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(2-pyren-1-ylethynyl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 1207741-27-2
• 化学式: C₃₉H₃₀O₅
• 分子量: 578.664
• InChiKey: FZJMDFANBQJTKY-SEFMXRCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1β-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose 、 1-溴芘 在 2-双环己基膦-2',6'-二甲氧基联苯 、 双(乙腈)氯化钯(II) 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以36%的产率得到1-[(1-pyrenyl)ethynyl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-β-D-ribofuranose
  参考文献：
  名称：

  Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides

  摘要：

  An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.030

文献信息

• Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides
  作者：Tomáš Bobula、Michal Hocek、Martin Kotora

  DOI：10.1016/j.tet.2009.11.030

  日期：2010.1

  An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.