A new type of artificial glycolipid constituted with 2-acetamido-2-deoxy-β-D-mannuronic acid was synthesized utilizing a readily accessible building block, methyl 2-(benzoyloxy)iminoglycosuronate as the glycosyl donor. Stereocontrolled β-glycosidation of the donor was as smoothly effected as the subsequent stereospecific reduction of (benzoyloxy)imino function. After anomeric activation, attachment of the spacer (2-aminoethanol)-linked stearic acid and final deblocking gave the designed glycolipid in good overall yield.
我们利用一种容易获得的结构单元--2-(苯甲酰氧基)亚
氨基糖苷酸甲酯作为糖基供体,合成了一种由 2-乙酰
氨基-2-脱氧-β-
D-甘露糖酸构成的新型人工
糖脂。供体的立体定向 β-糖苷化与随后的(苯甲酰氧基)亚
氨基功能的立体定向还原一样顺利。经过异构活化、连接间隔物(2-
氨基
乙醇)-连接
硬脂酸和最终解锁,就得到了所设计的
糖脂,而且总收率很高。