Allyl-tetra-O-acetyl-β-D-glucopyranoside (CAS 10343-15-4)

Allyl-tetra-O-acetyl-β-D-glucopyranoside is a glycosyl donor widely utilized in synthetic carbohydrate chemistry and glycosylation studies. This acetyl-protected glucopyranoside serves as a crucial intermediate in the synthesis of more complex oligosaccharides and glycoconjugates. Its allyl group allows for selective deprotection and further functionalization, making it a versatile building block for the assembly of glycan structures. In research, allyl-tetra-O-acetyl-β-D-glucopyranoside is used to investigate glycosylation mechanisms, particularly the formation of glycosidic bonds under various catalytic conditions. It aids in exploring the stereoselectivity of glycosylation reactions, providing insights into the factors that influence the α- or β-selectivity in glycoside synthesis. This compound is also employed in the development and optimization of glycosylation protocols, contributing to the synthesis of biologically relevant glycans for structural and functional studies. Furthermore, its acetyl-protected form enhances its stability and solubility, facilitating its use in diverse reaction conditions. Researchers use allyl-tetra-O-acetyl-β-D-glucopyranoside to synthesize glycomimetics and glycoconjugates that can be employed in studying carbohydrate-protein interactions, cell surface recognition, and signal transduction processes. Its role in these applications underscores its importance in advancing carbohydrate research and developing new tools for glycoscience.