((2R,3S,6S)-6-cyclohexenyl-2-((ethoxycarbonyloxy)methyl)-3,6-dihydro-2H-pyran-3-yl)methyl ethyl carbonate | 1336911-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ((2R,3S,6S)-6-cyclohexenyl-2-((ethoxycarbonyloxy)methyl)-3,6-dihydro-2H-pyran-3-yl)methyl ethyl carbonate
• 英文别名: [(2R,3S,6S)-6-(cyclohexen-1-yl)-3-ethoxycarbonyloxy-3,6-dihydro-2H-pyran-2-yl]methyl ethyl carbonate
• CAS: 1336911-24-0
• 化学式: C₁₈H₂₆O₇
• 分子量: 354.4
• InChiKey: PUANWDHGSSXHMB-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-环状己烯三氟甲烷磺酸 、 3,4,6-tri-O-ethoxycarbonyl-D-glucal 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基氯化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以80%的产率得到((2R,3S,6S)-6-cyclohexenyl-2-((ethoxycarbonyloxy)methyl)-3,6-dihydro-2H-pyran-3-yl)methyl ethyl carbonate
  参考文献：
  名称：

  Palladium Catalyzed Stereoselective C-Glycosylation of Glycals with Enol Triflates

  摘要：

  An efficient palladium catalyzed C-glycosylation of glycals with enol triflates has been established. The coupling reactions took place on the anomeric carbon, and the coupling products gave exclusively a isomers. The flexibility of the reaction was exemplified by the broad spectra of substrate scope, constituted of glycals protected with good leaving groups as well as an assortment of enol triflates.

  DOI：

  10.1021/ol202368n

文献信息

• Palladium Catalyzed Stereoselective <i>C</i>-Glycosylation of Glycals with Enol Triflates
  作者：Yaguang Bai、Minli Leow、Jing Zeng、Xue-Wei Liu

  DOI：10.1021/ol202368n

  日期：2011.10.21

  An efficient palladium catalyzed C-glycosylation of glycals with enol triflates has been established. The coupling reactions took place on the anomeric carbon, and the coupling products gave exclusively a isomers. The flexibility of the reaction was exemplified by the broad spectra of substrate scope, constituted of glycals protected with good leaving groups as well as an assortment of enol triflates.