3,4,6-tri-O-ethoxycarbonyl-D-glucal | 1336911-25-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 3,4,6-tri-O-ethoxycarbonyl-D-glucal
• 英文别名: [(2R,3S,4R)-3,4-bis(ethoxycarbonyloxy)-3,4-dihydro-2H-pyran-2-yl]methyl ethyl carbonate
• CAS: 1336911-25-1
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: BDHNXIMKNXECSB-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-ethoxycarbonyl-D-glucal 、 苯肼 在 1,10-菲罗啉 、 氧气 、 palladium diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以43%的产率得到((2R,3S,6S)-6-phenyl-2-((ethoxycarbonyloxy)methyl)-3,6-dihydro-2H-pyran-3-yl)methyl ethyl carbonate
  参考文献：
  名称：

  Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation

  摘要：

  An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure alpha-C-glycosides were obtained when (3R)-glycals were employed, whereas alpha,beta mixtures were observed with (3S)-glycals.

  DOI：

  10.1021/jo401032r

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.
• Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed <i>C</i>-Glycosylation
  作者：Yaguang Bai、Le Mai Hoang Kim、Hongze Liao、Xue-Wei Liu

  DOI：10.1021/jo401032r

  日期：2013.9.6

  An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure alpha-C-glycosides were obtained when (3R)-glycals were employed, whereas alpha,beta mixtures were observed with (3S)-glycals.