Institute of Chemistry
Topic
Application of methyl thioglycolate as an activating-protecting group of monosaccharides in oligosaccharide synthesis
PhD. program
Organic chemistry
Year of admission
2025
Name of the supervisor
Ing. Maroš Bella, PhD.
Contact:
Receiving school
Faculty of Natural Sciences, Comenius University Bratislava
Annotation
In synthesis of oligosaccharides, thioglycosides of suitably protected monosaccharides are widely used as glycosyl donors. The idea of this project is to combine thioglycosylation of monosaccharides with subsequent protection of the 2-O-hydroxyl group by cyclization with the S-aglycone moiety to form a bicyclic intermediate. The goal of the doctoral research project is to investigate the thioglycosylation of peracetylated penta- and hexapyranoses with methyl thioglycolate followed by lactonization of the methyl ester aglycone with the 2-O-hydroxyl group. Further manipulation of the protecting groups should enable a more efficient preparation of orthogonally protected monosaccharides, which should find applications in oligosaccharide synthesis. The established synthetic protocols will also be extended to partially protected monosaccharides to further increase synthetic efficiency.