Benzyl 2,3,6-Tri-O-benzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside (CAS 182760-13-0)

Benzyl 2,3,6-Tri-O-benzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside is a highly specialized synthetic molecule extensively used in the field of carbohydrate chemistry for studying and developing glycosylation reactions, particularly in the synthesis of complex glycostructures. The molecule′s structure includes benzyl groups at the 2, 3, and 6 positions and a trifluoromethanesulfonyl (triflate) group at the 4 position. These protective groups are pivotal as they enhance the molecule′s stability and reactivity, allowing for selective activation and subsequent glycosidic bond formation with various nucleophiles. This compound is primarily utilized in the synthesis of β-linked galactosides, where the triflate group acts as a leaving group during the formation of the glycosidic bond. Its role in facilitating the selective and efficient formation of glycosidic linkages under mild conditions makes it invaluable in synthesizing biologically relevant oligosaccharides and glycoconjugates. Researchers leverage this chemical to explore the stereochemical outcomes of glycosylations and to refine the methodologies for assembling carbohydrates with specific and desired configurations. In scientific research, Benzyl 2,3,6-Tri-O-benzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside is also employed in mechanistic studies to understand the kinetics and dynamics of enzymatic processes involving glycosyltransferases. These applications are critical for advancing our knowledge of carbohydrate chemistry and for developing new synthetic strategies in glycoscience.