Radboud University , Institute for Molecules and Materials , Heyendaalseweg 135 , Nijmegen 6525 AJ , The Netherlands.
J Org Chem. 2019 Apr 5;84(7):4486-4500. doi: 10.1021/acs.joc.9b00022. Epub 2019 Mar 7.
Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.
立体选择性糖基化仍然是寡糖化学合成的主要挑战。在此，我们报告了一种通过分子内烷基化反应将硫代糖苷转化为β-锍离子的简单方法，从而实现了各种糖基受体的高度α-选择性糖基化。我们研究了硫代糖苷取代基和保护基模式对糖基给体的影响，发现其与观察到的立体选择性有明显的相关性。
