2,3,4-Tri-O-benzyl-1-S-ethyl-β-L-thiofucopyranoside (CAS 99409-34-4)

2,3,4-Tri-O-benzyl-1-S-ethyl-β-L-thiofucopyranoside is a thiofucoside derivative used extensively in synthetic carbohydrate chemistry for the construction of complex oligosaccharides and glycoconjugates. The compound is characterized by its sulfur atom replacing the oxygen in the glycosidic bond, conferring enhanced stability against hydrolysis. The benzyl protecting groups on the hydroxyl functionalities ensure its solubility and stability, facilitating its use in various glycosylation reactions. In research, 2,3,4-Tri-O-benzyl-1-S-ethyl-β-L-thiofucopyranoside is employed to study glycosylation mechanisms, particularly focusing on the formation and stereoselectivity of glycosidic bonds. The thio linkage allows for the selective activation of the glycosyl donor under mild conditions, often utilizing promoters such as N-iodosuccinimide (NIS) and silver triflate (AgOTf). This compound is essential in synthesizing fucose-containing oligosaccharides, which are crucial for exploring the role of fucosylation in biological processes such as cell-cell recognition, signal transduction, and immune response modulation. Additionally, it is used to develop glycomimetics that mimic the structure and function of natural glycans, aiding in the study of carbohydrate-protein interactions and the development of enzyme inhibitors. The stability and versatility of 2,3,4-Tri-O-benzyl-1-S-ethyl-β-L-thiofucopyranoside make it a valuable tool for advancing glycoscience and understanding the complex dynamics of glycosylation.