Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri, 63121, USA.
Chemistry. 2020 Jun 26;26(36):8053-8063. doi: 10.1002/chem.201905576. Epub 2020 Jun 2.
Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag O.
在发现银（I）氧化物促进的糖基溴化物的糖基化反应在催化 TMSOTf 或 TfOH 的存在下可以大大加速后，我们在此报告了一个新发现，即在这些反应条件下，糖基氯甚至是更有效的糖基供体。所开发的反应条件与各种糖基氯配合良好。苯甲酰基和苄基氯都已成功糖苷化，并且这些反应条件在与氮和硫原子的偶联底物的结合中证明是有效的。这种糖苷化的另一个方便的特点是反应的进展可以通过肉眼监测；通过 AgO 的特征暗颜色的消失可以判断反应的完成。
