Synthesis of Thiosugars and Disaccharides

Abstract

Thioglycosylation, a versatile synthetic method for the formation of glycosidic bonds using thioglycosides as donors, has emerged as a powerful tool in carbohydrate chemistry. This abstract provides an overview of thioglycosylation reactions, their underlying chemistry, diverse applications, and future perspectives. Thioglycosylation reactions involve the activation of a glycosyl acceptor and a thioglycoside donor, followed by the formation of a glycosidic bond through nucleophilic substitution or activation of the glycosyl acceptor. The choice of activation method, protecting groups, and reaction conditions significantly influence the efficiency and regioselectivity of thioglycosylation reactions. Thioglycosylation has found widespread applications in the synthesis of complex carbohydrates, glycoconjugates, and glycomimetics with tailored properties. These include the preparation of oligosaccharides, glycopeptides, glycolipids, and glycoconjugate vaccines for biological studies and therapeutic interventions. Moreover, thioglycosylation plays a pivotal role in the synthesis of glycosylated natural products, pharmaceuticals, and materials with diverse functionalities. Recent advances in thioglycosylation methodologies, such as the development of novel glycosyl donors, catalysts, and reaction conditions, have expanded its synthetic scope and improved its efficiency and selectivity. Furthermore, the integration of thioglycosylation with other synthetic strategies, including enzymatic glycosylation and chemical ligation, offers exciting opportunities for the rapid assembly of complex glycostructures and glycoconjugates. Looking ahead, thioglycosylation holds great promise for addressing key challenges in glycobiology, drug discovery, and materials science. Future research directions may focus on the development of more efficient and sustainable thioglycosylation methodologies, the exploration of new glycosyl donors and acceptors, and the application of thioglycosylation in emerging fields such as glycoengineering and glycotherapy. In conclusion, thioglycosylation represents a valuable synthetic tool for constructing glycosidic linkages and synthesizing diverse glycoconjugates with biological and material applications. Continued research efforts in thioglycosylation chemistry are poised to yield novel insights, methodologies, and applications, driving innovation and discovery in carbohydrate science and beyond. In this project I have aimed to synthesize Thio glycosides with different furanose sugars and decode the underlying mechanism of the glycosylation reaction by 7 identifying the side products. For this I have used a pyridine sugar carbonate donor system of different Furanose sugars and a Thio-acceptors. The thioglycosylation reaction was carried out using TMSOTf as a Lewis acid to activate the donor system. Different conditions were tested to optimise the reaction and side product was identified to give insights into the reaction mechanism. In this project, the aim is to devise a reliable and enduring synthetic method for producing a range of Thioglycosides derived from furanose.