Automated continuous flow production of glycosylation ready monosaccharides

The production of suitably protected monosaccharides ready for chemical glycosylation is arguable one of the most time consuming processes in oligosaccharide synthesis. This is especially true in the case of "unusual" sugars that are not commercially available, such as those from secondary metabolites and prokaryotes. Here we demonstrate that a continuous flow platform permits the functionalization of monosaccharides on much faster time scales than is possible in conventional batch synthesis. By telescoping several reactions into a single sequence, this approach permits the construction of protected monosaccharides from commercially available precursors in mere hours. Furthermore, since many redox chemistries are amenable to continuous flow processing, this system permits the rapid synthesis of unusual sugars that otherwise require a week or more to construct in batch. The ability to interface this inexpensive system with the python-based open source MechWolf system to permit full automation will also be discussed.