3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-oxo-2-phenyl-4H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 1309445-41-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-oxo-2-phenyl-4H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS: 1309445-41-7
• 化学式: C₄₃H₄₆O₂₂
• 分子量: 914.825
• InChiKey: YTRZLGGILOOJEO-GCTOYHEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  65.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  277.53
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为产物：
  描述：

  7-羟基黄烷醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 C₁₆H₂₈AgN₄⁽¹⁺⁾ 、 苄基三乙基氯化铵 作用下， 反应 3.33h， 生成 7-hydroxy-4-oxo-2-phenyl-4H-chromen-3-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 、 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-oxo-2-phenyl-4H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids

  摘要：

  We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-alpha-D-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-beta-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.03.007