(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1239457-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(trifluoromethyl)phenoxy]oxan-2-yl]methyl acetate
• CAS: 1239457-40-9
• 化学式: C₂₁H₂₃F₃O₁₀
• 分子量: 492.403
• InChiKey: HDAOBUXZAZBXBK-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  对三氟甲基苯酚 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 氯化(1-丁基-3-甲基咪唑) 、 silver carbonate 作用下， 反应 0.75h， 以44%的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  卤化物熔盐作为O-糖苷键形成新反应介质的应用

  摘要：

  在这项研究中，我们探索了卤化物熔盐作为在碱性条件和温和加热下形成 O-糖苷键的反应介质的应用。在对硝基苯酚与乙酰溴-α-D-半乳糖的糖苷化反应中筛选出十八种不同的室温离子液体和熔融盐，代表四种不同类别的阳离子（即咪唑鎓、吡啶鎓、吡咯烷鎓和铵）。1-丁基-4-甲基咪唑鎓氯化物（BMIM·Cl）得到了最好的结果，并将其应用于其他酚类底物的反应中，产率高达80%。所有反应都对β-端基异构体具有高度选择性，并且熔融盐BMIM·Cl可以很容易地重复使用而不会明显降低活性。

  DOI：

  10.1002/ejoc.201000188

文献信息

• O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids
  作者：Ian Jamie Talisman、Vineet Kumar、Jacqueline Razzaghy、Sanjay V. Malhotra

  DOI：10.1016/j.carres.2011.03.007

  日期：2011.5

  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.