3,4,6-tri-O-acetyl-2-deoxy-1-O-(diphenylphosphoryl)-α-D-arabino-hexopyranose | 145828-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-1-O-(diphenylphosphoryl)-α-D-arabino-hexopyranose
• 英文别名: [(2R,3S,4R,6R)-3,4-diacetyloxy-6-[oxido(diphenoxy)phosphaniumyl]oxyoxan-2-yl]methyl acetate
• CAS: 145828-18-8
• 化学式: C₂₄H₂₇O₁₁P
• 分子量: 522.446
• InChiKey: BEBZMQIGFPKPRL-YCAMKHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-1-O-(diphenylphosphoryl)-α-D-arabino-hexopyranose 、 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 magnesium(II) perchlorate 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以49%的产率得到
  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：

  氯磷酸二苯酯 在 N-甲基咪唑 、 氢溴酸 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 32.25h， 生成 3,4,6-tri-O-acetyl-2-deoxy-1-O-(diphenylphosphoryl)-α-D-arabino-hexopyranose
  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