Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate (CAS 62812-42-4)

Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate is a synthetic carbohydrate derivative used extensively in glycosylation and carbohydrate chemistry research. Its structure contains three acetyl groups protecting the hydroxyls at positions 2, 3, and 4, while the thio-beta-D-glucopyranoside unit mimics a glucuronic acid derivative. The thio functionality at the anomeric position provides enhanced stability and reactivity, making this compound an excellent glycosyl donor in thioglycoside-mediated glycosylation reactions. Researchers primarily use this compound to synthesize oligosaccharides and glycoconjugates due to its robust glycosyl donor properties. The phenylthio group ensures efficient glycosidic bond formation, crucial for creating structurally diverse glycans. The acetyl protections stabilize the molecule and allow regioselective deprotection, facilitating subsequent functionalization. This enables the stepwise assembly of complex oligosaccharides that resemble naturally occurring glycans. Moreover, the uronic acid functionality plays a significant role in the synthesis of glycosaminoglycan-like structures and other acidic polysaccharides. These glycoconjugates are essential for studying protein-carbohydrate interactions, particularly with glycosyltransferases and lectins. Through the strategic use of this compound, researchers can investigate the specificity of carbohydrate recognition and the biosynthetic pathways of acidic glycan structures, advancing the understanding of glycan biology and the development of carbohydrate-based tools.