2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N′,N′-Tetramethylphosphorodiamidate (ca. 20% in Benzene) (CAS 143520-19-8)

2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N′,N′-tetramethylphosphorodiamidate is a glycosyl donor frequently used in carbohydrate synthesis due to its versatile structure and activating phosphorodiamidate group. The benzyl groups offer stable protection of the hydroxyls on the glucopyranosyl ring, while the phosphorodiamidate moiety provides a strong leaving group that stabilizes the glycosylation intermediate, enhancing the efficiency of glycosyl transfer. This unique combination enables stereoselective glycosylation reactions, allowing for the targeted synthesis of specific glycosidic linkages crucial in complex carbohydrate construction. In recent research, this compound has been instrumental in synthesizing oligosaccharides, glycoconjugates, and other carbohydrate derivatives with precisely controlled structures. It has facilitated the formation of both alpha and beta glycosidic bonds, contributing to our understanding of enzyme specificity and substrate recognition. By providing a stable intermediate during glycosidic bond formation, it has allowed scientists to explore the subtleties of glycan biosynthesis, elucidating the enzymatic steps involved in glycosyltransferase activity. Furthermore, its benzyl protection is removable via catalytic hydrogenolysis, offering clean deprotection of the final glycan product. Overall, this compound serves as a valuable tool in synthetic glycoscience, enabling researchers to delve deeper into glycan structure-function relationships.