Methyl 4,6-O-Benzylidene-α-D-glucopyranoside (CAS 14155-23-8)

Methyl 4,6-O-Benzylidene-α-D-glucopyranoside is a carbohydrate derivative used extensively in research to investigate glycosylation pathways and the roles of glucose residues in glycan synthesis. The benzylidene protection at the 4,6 positions forms a cyclic acetal that stabilizes the structure and allows selective deprotection, while the methyl group on the anomeric carbon fixes the glycoside in the α-configuration. This enables researchers to control and direct glycosylation reactions, providing valuable insight into enzyme specificity and kinetics. In glycosylation research, this compound serves as a protected glucose derivative in glycosyltransferase assays and glycan synthesis protocols. It facilitates the study of enzymatic pathways involved in glucose-based oligosaccharide formation and modification, particularly those requiring the α-configuration for recognition. It is also employed in the synthesis of various complex glycans, where selective deprotection and substitution patterns are essential. The compound acts as a building block for preparing oligosaccharides that can mimic natural glycan structures, allowing scientists to probe carbohydrate-binding proteins like lectins and glycosidases for specificity and binding affinity. Overall, Methyl 4,6-O-Benzylidene-α-D-glucopyranoside is crucial in research aiming to explain the mechanisms underlying glycan-protein interactions and the biosynthesis of glucose-containing oligosaccharides.