L-阿拉伯吡喃糖1,2-cis-糖苷化反应的研究

Research of L-arabinopyranosyl 1,2-cis-glycosylation

目的设计一个合理有效的供体来构建L-阿拉伯吡喃糖1,2-cis-苷键。方法以L-阿拉伯糖为原料,制备了3个乙硫苷供体,在不同温度、溶剂条件下,对供体进行糖苷化反应的考察。结果 3,4-位双苯甲酰基取代的供体Ⅱa以最佳的立体选择性和收率得到β-糖苷化产物,产物的结构经1HNMR分析确证。结论所用方法的条件温和、操作简便、立体选择性好、收率高。

OBJECTIVE To design a useful donor for building L - arabinopyranosyl 1,2 - c/s - glycosidic bond. METHODS Starting from L- arabinose,three thioglycoside donors were prepared for glycosylation under different temperatures and solvents. RFSULTS 3,4 - di - benzoyl protected donor afforded β - glycoside with the best steroselectivity and yield, and all synthetic compounds were confirmed by 1HNMR. CONCLUSION The method has the characteristic of mild conditions, simple operation, high steroselectivity and yield.