Microfluidics-Based Ionic Catch and Release Oligosaccharide Synthesis (ICROS-Microflow) to Expedite Glycosylation Chemistry

A continuous microfluidic glycosylation strategy that requires no chromatography between steps and significantly expedites glycosylation chemistry is described. This practical approach incorporates the advantages of imidazolium-based chromatography-free purification and in situ mass spectrometry reaction monitoring to achieve fast reaction optimization and shorter reaction times. We demonstrate the utility of this strategy in the synthesis of a series of glycoside targets, including an α-(1,6)-trimannoside and a branched Man₅ oligomannoside, within 1 day.