Selective electrochemical glycosylation by reactivity tuning
Selective electrochemical glycosylation by reactivity tuning
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DOI：
10.1039/b316728c
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发表时间：
2004-01-01
影响因子：
3.2
通讯作者：
Wadhawan, JD
中科院分区：
文献类型：
--
作者：
France, RR;Compton, RG;Wadhawan, JD
硒代糖苷供体的电化学糖基化在乙腈中的未分裂细胞中有效进行，产生 β-糖苷。对选定的硒代、硫代和O-糖苷的循环伏安图的测量表明氧化电位对异头取代基的依赖性，从而可以通过利用可变电池电位的选择性电化学激活结合糖基供体的反应性调节来快速构建寡糖。多种二糖很容易以高产率合成，但使用硒代糖苷作为糖基供体对硫代糖苷受体进行选择性糖基化的局限性暴露出来。描述了第一个电化学三糖合成。
Electrochemical glycosylation of a selenoglycoside donor proceeds efficiently in an undivided cell in acetonitrile to yield beta-glycosides. Measurement of cyclic voltammograms for a selection of seleno-, thio-, and O-glycosides indicates the dependence of oxidation potential on the anomeric substituent allowing the possibility for the rapid construction of oligosaccharides by selective electrochemical activation utilising variable cell potentials in combination with reactivity tuning of the glycosyl donor. A variety of disaccharides are readily synthesised in high yield, but limitations of the use of selenoglycosides as glycosyl donors for selective glycosylation of thioglycoside acceptors are exposed. The first electrochemical trisaccharide synthesis is described.