4-iodophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 1364510-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-iodophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: [(3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-iodophenoxy)oxan-3-yl] acetate
• CAS: 1364510-85-9
• 化学式: C₁₇H₁₉IO₈
• 分子量: 478.238
• InChiKey: ODDYORMDUHOQPF-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-iodophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 四丁基溴化铵 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以94%的产率得到4,4'-bis-(2,3,4-tri-O-acetyl-β-D-xylopyranosyloxy)biphenyl
  参考文献：
  名称：

  Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides

  摘要：

  A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.

  DOI：

  10.1021/jo2025652
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide 、 4-碘苯酚 在 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 以2.31 g的产率得到4-iodophenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides

  摘要：

  A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.

  DOI：

  10.1021/jo2025652

文献信息

• Xylose derivatives and process for preparation thereof
  申请人：National Taipei University of Technolog

  公开号：US10385087B1

  公开（公告）日：2019-08-20

  Disclosure of the present invention relates to a method for synthesis of a xylose derivative, which comprises protecting a xylose with a protective group, followed by incorporating to a halogen atom as a leaving group; removing the protective groups and using water-soluble ligands to carry out a Suzuki cross-couplings reaction with a palladium catalyst in a water solution. Ten new xylose derivatives as obtained by the method are also provided.

  本发明的公开涉及一种合成木糖衍生物的方法，该方法包括用保护基团保护木糖，然后将卤素原子作为离去基团引入；移除保护基团，并使用水溶性配体在水溶液中以钯催化剂进行铃木交叉偶联反应。本发明还提供了通过该方法获得的十个新的木糖衍生物。