用糖基化反应分离4半乳糖基-2-叠氮-2-脱氧甘露糖1-硝酸酯及其葡萄糖型异构体

Separation of 4 galactosyl -2-azido -2-deoxy mannose 1-nitrate and corresponding glucose type isomer by glycosylation

目的 :分离两种极性极为相似的寡糖异构体并对一种新的糖基化方法进行初步探索。方法 :用乳糖烯叠氮硝化反应产物———葡萄糖型硝酸酯和甘露糖型硝酸酯的混合物作供体进行糖基化反应 ,选择性地合成甘露糖型衍生物 ,并分离出葡萄糖型硝酸酯。结果 :高收率、高立体选择性地合成了 8个甘露糖苷及糖酯 ,分离出较纯净的葡萄糖型硝酸酯。结论 :对于两种极性极为相近的寡糖异构体 ,可利用二者糖基化能力的差异将二者分开 ;糖基硝酸酯作供体可提供一条合成 2 氨基 2

To separate two oligosaccharide isomers which have very similar polarity and to try a new method of glycosylation. Methods: Some mannose type derivatives can be prepared selectively by glycosylation of a mixture of mannose type 1 nitrate and corresponding glucose type isomer, which is obtained from azidonitration of lactal. In the mean time, glucose type 1 nitrate can be separated. Results: Eight mannose type α glycosides and esters were synthesized stereoselectively in high yields and pure glucose type 1 nitrate was recovered. Conclusion: Two oligosaccharide isomers which had the same polarity could be separated according to their difference of olycosylation reactivity; It may offer a new path to sythesize 2 amino 2 deoxy oligosaccharides by using glycosyl 1 nitration as donor.