摘要
To investigate a new glycosylation method. Methods In the presence of TMSOTfas catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with aseries of carboxylic acid, phenols, alcohols and saccharides respectively to give the correspondingglycosylation products. The compounds were determined by ~1H NMR and ^(13)C NMR spectra. ResultsThe α-glu-co-pyranosides and related oligosaccharides were prepared in high yields. Conclusion The3, 5-dinitro-benzoyl group was found to be a good leaving group at the anomeric position andO-glucopyranosides and oligosaccharides were stereoselectively synthesized in good yield.
目的 探索一种新型的糖基化方法。方法 以TMSOTf为催化剂 ,1 α O (3,5 二硝基苯甲酰基 ) 2 ,3,4 ,6 四 O 苄基 D 吡喃葡萄糖分别与一系列的羧酸、酚、醇和单糖反应 ,得到糖基化产物 ,采用1 H、1 3CNMR谱确证了产物的构型。结果高立体选择性、较好收率地得到了α 葡萄糖苷和相应的寡糖。结论 3,5 二硝基苯甲酰氧基作为良好的糖端基离去基用于寡糖的合成 ,具有反应条件温和、收率较高、立体选择性好的特点。
基金
NationalNaturalScienceFoundationofChina(2 0 3 72 0 0 3 ,3 0 3 3 0 690 ) .
