Isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (CAS 114967-51-0)

Isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside is a benzyl-protected glucopyranoside extensively used in synthetic carbohydrate chemistry. This compound is valuable for its role in the construction of complex oligosaccharides and glycoconjugates. The benzyl protecting groups on the hydroxyl functionalities enhance its stability and solubility, making it suitable for various glycosylation reactions. In research, isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside is employed to study the mechanisms of glycosylation, focusing on the formation of glycosidic bonds under different catalytic conditions. The isopropyl group facilitates selective deprotection, allowing for the sequential assembly of carbohydrate chains. Researchers use this compound to investigate the stereoselectivity of glycosylation reactions, providing insights into factors influencing α- or β-selectivity. This compound is also crucial in synthesizing glycomimetics and functionalized glycans, which are essential for studying carbohydrate-protein interactions, cell surface recognition, and signal transduction processes. Its utility extends to the development of inhibitors for glycan-processing enzymes and exploring the structural and functional roles of glucosyl residues in biological systems. The compound′s versatility in synthetic applications highlights its importance in advancing the understanding of glycoscience and enabling the synthesis of well-defined glycan structures for structural and functional studies.