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目的研究8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷的合成。方法以草酰乙酸和D-阿拉伯糖为原料,通过cornforth反应、乙酰化、甲酯化、烯醇化、脱乙酰基、硅基化、碳酸酯化等7步反应制备目标化合物。结果与结论与文献谱图进行对照,确证目标化合物的结构,7步反应的总收率为22%,化合物的立体选择性较高,方法操作简单、易于实施,为含(2→7)苷键结构的Kdo寡糖制备奠定了基础。
Aim To study the synthesis of 8-oxo-t-butyldimethylsilyl-4,5-oxo-carbonyl-3-deoxy-β-D-manno-2-octylcophanate allylglycoside. Methods The target compound was prepared from oxaloacetic acid and D-arabinose by 7 steps, such as cornforth reaction, acetylation, methyl esterification, enolase, deacetylation, silylation and carbonate esterification. The results and conclusions were compared with the literature. The structure of the target compound was confirmed. The overall yield of the 7-step reaction was 22% and the stereoselectivity of the compound was high. The method was simple and easy to implement. The key structure of Kdo oligosaccharide preparation laid the foundation.