benzyl 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-β-L-rhamnopyranoside | 202717-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-β-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,6S)-5,5-difluoro-4-methoxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 202717-83-7
• 化学式: C₂₁H₂₂F₂O₅
• 分子量: 392.399
• InChiKey: WIERVCGMXDEAIM-DEYWJSPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-β-L-rhamnopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-α-L-rhamnopyranose 、 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-β-L-rhamnopyranose
  参考文献：
  名称：

  An Improved Synthesis of 4-O-Benzoyl-2,2-difluorooleandrose from l-Rhamnose. Factors Determining the Synthesis of 2,2-Difluorocarbohydrates from 2-Uloses

  摘要：

  4-O-Benzoyl-2,2-difluorooleandrose (16) has been synthesized from L-rhamnose. The key steps are the formation of a difluoromethylene group in 12 by reacting ulose 11 with DAST and the chemoselective methylation of diol 13 to give compound 14. To obtain the 2,2-difluoro compound 12, the substituents in the neighborhood of the carbonyl group in ulose 11 must be equatorial and the sugar ring must have restricted conformational mobility. This was done using 1,1,2,2-tetramethoxycyclohexane (TMC) to protect the hydroxyls at positions 3 and 4 in the sugar ring.

  DOI：

  10.1021/jo971846x
• 作为产物：
  描述：

  benzyl 2-deoxy-2,2-difluoro-β-L-rhamnopyranoside 在 4-二甲氨基吡啶 、 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 benzyl 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  An Improved Synthesis of 4-O-Benzoyl-2,2-difluorooleandrose from l-Rhamnose. Factors Determining the Synthesis of 2,2-Difluorocarbohydrates from 2-Uloses

  摘要：

  4-O-Benzoyl-2,2-difluorooleandrose (16) has been synthesized from L-rhamnose. The key steps are the formation of a difluoromethylene group in 12 by reacting ulose 11 with DAST and the chemoselective methylation of diol 13 to give compound 14. To obtain the 2,2-difluoro compound 12, the substituents in the neighborhood of the carbonyl group in ulose 11 must be equatorial and the sugar ring must have restricted conformational mobility. This was done using 1,1,2,2-tetramethoxycyclohexane (TMC) to protect the hydroxyls at positions 3 and 4 in the sugar ring.

  DOI：

  10.1021/jo971846x