Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside (CAS 187022-49-7)

Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is a thioglycoside derivative notable for its role as a glycosyl donor in carbohydrate synthesis. The thioglycoside group enhances its stability, allowing selective activation under mild conditions. The acetyl protecting groups on the hydroxyl functionalities make it suitable for complex glycosylation reactions by preventing undesired side reactions. Researchers have used this compound in glycosylation reactions for synthesizing oligosaccharides, glycopeptides, and other glycoconjugates. Its reactivity is enhanced by the trichloroethoxyformamido group, enabling precise control over glycosidic bond formation. The beta-anomeric configuration is instrumental in stereoselective synthesis, providing high fidelity in product structures. Its acetylated hydroxyls and trichloroethoxyformamido group protect against unwanted substitutions while still allowing selective deprotection. In the field of glycoscience, this chemical has been used to generate complex glycans for studying protein-glycan interactions and glycosylation pathways. The defined stereochemistry of the beta-glycoside provides insight into enzyme-substrate specificities. Furthermore, it has helped explain glycosyltransferase mechanisms by providing well-defined substrates. Its use in synthetic biology has aided in constructing carbohydrate-based tools for investigating cell signaling and recognition processes, crucial in carbohydrate chemistry.