2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl thiocyanate | 1392843-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl thiocyanate
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-thiocyanatooxan-2-yl]methyl benzoate
• CAS: 1392843-78-5
• 化学式: C₃₅H₂₇NO₉S
• 分子量: 637.667
• InChiKey: FPAJLUHHLVBFBZ-XFUYZNCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl thiocyanate 在 四丁基溴化铵 、 2-hydroxy-N.N,N-tributylethanammonium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2,3,4,6-Tetra-O-benzoyl-α-D-galactopyranosyl isothiocyanate 、 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl thiocyanate 、 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl isothiocyanate
  参考文献：
  名称：

  Influence of bromide ions on the synthesis of anomeric thiocyanates

  摘要：

  The synthesis of anomeric thiocyanates with the alpha- and beta-configuration is described. Reactions performed under standard conditions afforded the 1,2-trans derivatives as the main products, whereas in the presence of the quaternary ammonium salts, the 1,2-cis-thiocyanates were formed preferentially. The strong influence of the bromide ions on the distribution of the products is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.068