3,4-Di-O-benzyl-1,2,6-tri-O-acetyl-α-D-mannopyranose (CAS 65827-57-8)

3,4-Di-O-benzyl-1,2,6-tri-O-acetyl-α-D-mannopyranose is a chemically modified derivative of mannose that is extensively used in synthetic carbohydrate chemistry for the construction of complex glycostructures. The molecule is particularly noteworthy for its strategic protective groups—benzyl groups at the 3 and 4 positions and acetyl groups at the 1, 2, and 6 positions—which effectively shield reactive hydroxyl groups and allow for selective chemical reactions at other sites. This selective protection is critical for the stepwise assembly and modification of carbohydrates, enabling precise control over the synthesis of oligosaccharides and glycoconjugates. In research, this compound serves as a key intermediate in the synthesis of mannose-containing polysaccharides and glycoproteins, which are vital for studying biological recognition processes such as those involving lectins, which play crucial roles in immune response and cell-cell interactions. The α-configuration of the glycosidic bond is especially important, as it mirrors the natural orientation of mannose in many biological systems, providing accurate models for biological studies. Furthermore, the protected mannopyranose derivative is used to explore the enzymatic mechanisms of glycosylation, offering insights into the biosynthesis of glycosidic bonds and the role of specific enzymes in this process. The research involving 3,4-Di-O-benzyl-1,2,6-tri-O-acetyl-α-D-mannopyranose not only advances our understanding of carbohydrate chemistry but also contributes to the development of methodologies for synthesizing biologically relevant molecules.