We synthesized new chiral fluorescence labeling reagents having a 2,3-anthracenedicarboximide group from D-glucosamine, and it was possible to introduce target alcohols at the anomeric positions of the reagents with β-selectivity by glycosidations. Especially, it was possible to use methyl glycoside reagent as a glycosyl donor with a Lewis acid and microwave irradiation, and it gave selectively β-glycoside while the reaction without microwave irradiation gave α- and β-mixed glycosides. Those reagents showed very high chiral discrimination ability, and they made it possible to separate the eight stereoisomers of 4,8,12,16-tetramethylheptadecanol by HPLC after derivatizations.
我们合成了新的手性荧光标记试剂,这些试剂具有2,3-
蒽二羧
酰亚胺基,通过D-
氨基葡萄糖可以在试剂的亚糖位引入目标醇,并具有β选择性,采用糖苷化反应。特别地,可以使用甲基糖苷试剂作为糖基供体,结合
路易斯酸和微波辐射,使反应选择性生成β-糖苷,而未使用微波辐射的反应则生成α-和β-混合糖苷。这些试剂表现出非常高的手性辨别能力,使得在衍生化后可以通过高效
液相色谱分离出4,8,12,16-四甲基
庚醇的八种立体异构体。