Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl-β-D-glucopyranoside (CAS 80035-34-3)

Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl-β-D-glucopyranoside is a compound frequently utilized in synthetic organic chemistry for carbohydrate research and glycosylation studies. Its structure consists of a β-D-glucopyranoside core with a phthalimido group at the 2-position and protective benzyl groups at the 3-O and 4,6-O positions. These protective groups play a crucial role in controlling the reactivity and selectivity of the sugar molecule during glycosylation reactions. Specifically, the phthalimido moiety can be selectively removed under mild conditions to reveal a free amine group, allowing for further functionalization or conjugation with other molecules. In research, this compound has been extensively employed in the synthesis of complex oligosaccharides and glycoconjugates. By exploiting the reactivity of its functional groups, chemists can design and assemble diverse carbohydrate structures with precision. Additionally, it serves as a valuable tool for investigating glycosylation mechanisms and enzyme-substrate interactions. Researchers use this compound to probe the substrate specificity of glycosyltransferases and understand the molecular basis of carbohydrate recognition. Moreover, the synthetic strategies developed using this glycoside contribute to the advancement of carbohydrate-based materials, including biomaterials, sensors, and drug delivery systems, expanding its utility beyond fundamental research into broader scientific applications.