不同溶剂中氟原子对糖苷键立体选择性的影响

• 作 者: 韩小见 王佳佳 万玥 赵云燕 赵炜
• 机 构: 长治学院化学系,南开大学药学院,
• 出 处: 化学通报
• 发表日期: 2015年07期
• 关键词: 溶剂 2-氟苄基 溶剂效应 硫苷 立体选择性 苄基 供体 糖苷键 葡萄糖 糖基化

在乙腈等5种不同溶剂中,以2,3,4-O-三苄基-6-O-(2-氟苄基)-β-对甲基苯基-D-葡萄糖硫苷作为糖基供体,甲醇作为受体,并以糖基化供体2,3,4,6-O-四苄基-β-对甲基苯基-D-葡萄糖硫苷为对照,研究了在葡萄糖硫苷C-6位引入氟取代基对糖苷键立体选择性的影响。结果表明,引入的2-氟苄基与普通苄基保护基相比,β构型比例都有一定程度的提高,其中当溶剂为乙腈时,β构型比例较在其他溶剂中提升最明显,α/β比值可达到1/4.7。

2,3,4-O-tribenzyl-6-O- (2-fluorobenzyl) -β-p-methylphenyl-D-glucosidoside was used as a sugar base in five different solvents such as acetonitrile Donor and methanol as acceptor. The glycosylation donor 2,3,4,6-O-tetrabenzyl-β-p-methylphenyl-D-glucopyranoside was used as control. Effect of introduction of fluorine substituents on glycosidic bond stereoselectivity at C-6 position. The results showed that the β-configuration ratio of 2-fluorobenzyl group was improved to a certain extent compared with that of the common benzyl group. When the solvent was acetonitrile, the β-configuration ratio was the most obvious increase in other solvents, α / β ratio can reach 1 / 4.7.