3,5-di-O-benzoyl-2-O-(3-(trifluoromethyl)benzoyl)-α-D-ribofuranosyl bromide | 145828-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzoyl-2-O-(3-(trifluoromethyl)benzoyl)-α-D-ribofuranosyl bromide
• 英文别名: 3,5-di-O-benzoyl-2-O-[3-(trifluoromethyl)benzoyl]-α-D-ribofuranosyl bromide；[(2R,3R,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-2-bromooxolan-3-yl] 3-(trifluoromethyl)benzoate
• CAS: 145828-14-4
• 化学式: C₂₇H₂₀BrF₃O₇
• 分子量: 593.351
• InChiKey: OFQVQIOZEPHDOS-ODAXIHTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-2-O-(3-(trifluoromethyl)benzoyl)-α-D-ribofuranosyl bromide 在 六正丁基二锡 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Radical rearrangement of 2-O-(diphenylphosphoryl)glycosyl bromides. A new synthesis for 2-deoxy disaccharides and 2-deoxy ribonucleosides

  摘要：

  2-Deoxy-1-O-diphenylphosphoryl glycosides react with nucleophiles under mild conditions giving access to 2-deoxy disaccharides and nucleosides. The intermediate 2-deoxy-1-O-diphenylphosphoryl compounds were generated in situ by a radical 2 --> 1 migration of the phosphate ester group. This is the first observation of a rearrangement of a phosphate ester in radicals. ESR experiments and quenching of the radical at C2 by tin hydride or tin deuteride were used to detect the intermediates and to prove their structure.

  DOI：

  10.1021/jo00057a020
• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 在 吡啶 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3,5-di-O-benzoyl-2-O-(3-(trifluoromethyl)benzoyl)-α-D-ribofuranosyl bromide
  参考文献：
  名称：

  Radical rearrangement of 2-O-(diphenylphosphoryl)glycosyl bromides. A new synthesis for 2-deoxy disaccharides and 2-deoxy ribonucleosides

  摘要：

  2-Deoxy-1-O-diphenylphosphoryl glycosides react with nucleophiles under mild conditions giving access to 2-deoxy disaccharides and nucleosides. The intermediate 2-deoxy-1-O-diphenylphosphoryl compounds were generated in situ by a radical 2 --> 1 migration of the phosphate ester group. This is the first observation of a rearrangement of a phosphate ester in radicals. ESR experiments and quenching of the radical at C2 by tin hydride or tin deuteride were used to detect the intermediates and to prove their structure.

  DOI：

  10.1021/jo00057a020

文献信息

• Radical rearrangement of 2-O-(diphenylphosphoryl)glycosyl bromides. A new synthesis for 2-deoxy disaccharides and 2-deoxy ribonucleosides
  作者：Andreas Koch、Clemens Lamberth、Frank Wetterich、Bernd Giese

  DOI：10.1021/jo00057a020

  日期：1993.2

  2-Deoxy-1-O-diphenylphosphoryl glycosides react with nucleophiles under mild conditions giving access to 2-deoxy disaccharides and nucleosides. The intermediate 2-deoxy-1-O-diphenylphosphoryl compounds were generated in situ by a radical 2 --> 1 migration of the phosphate ester group. This is the first observation of a rearrangement of a phosphate ester in radicals. ESR experiments and quenching of the radical at C2 by tin hydride or tin deuteride were used to detect the intermediates and to prove their structure.