5-(((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-indole | 1344994-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-indole
• CAS: 1344994-70-2
• 化学式: C₄₂H₄₁NO₆
• 分子量: 655.791
• InChiKey: BMFQOQVCFRPEQL-QBLDGPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5-羟基吲哚 、 (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 在 Ag⁽¹⁺⁾*C₂₂H₂₄AgN₄⁽¹⁺⁾*2Cl^(1-) 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 5-(((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-indole 、
  参考文献：
  名称：

  Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

  摘要：

  We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl)imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the 13 isomer regardless of neighboring group effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.025