2-Pyridyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (CAS 105120-89-6)

2-Pyridyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside is a thio-linked glycosyl donor extensively used in carbohydrate synthesis and glycobiology research. This compound′s unique structure, featuring a thio-glycosidic bond and acetyl-protected hydroxyl groups, makes it an excellent intermediate for the construction of complex oligosaccharides and glycoconjugates. The thio linkage enhances its stability under various reaction conditions, making it suitable for glycosylation reactions. Researchers utilize this compound to investigate glycosylation mechanisms, focusing on the formation and selectivity of glycosidic bonds. Its pyridyl group allows for efficient activation and participation in glycosyl transfer reactions, often catalyzed by promoters like N-iodosuccinimide (NIS) or silver triflate (AgOTf). This specificity aids in exploring the stereoselectivity of glycosylation, providing insights into factors that influence α- or β-selectivity. In addition, it is employed in the synthesis of glycomimetics and functionalized glycans, which are crucial for studying carbohydrate-protein interactions, cell surface recognition, and immune responses. The acetyl protecting groups enhance its solubility and stability, facilitating its use in diverse reaction conditions. Overall, 2-Pyridyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside is a vital tool in advancing glycoscience, enabling the synthesis of complex carbohydrates and the study of their biological functions.