3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose (CAS 22529-61-9)

3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose is a chemically synthesized derivative of glucose, commonly used in carbohydrate chemistry for studying the behavior and manipulation of sugar molecules under synthetic conditions. This compound is specifically engineered with protective groups—benzyl and isopropylidene—that shield reactive hydroxyl groups and influence the reactivity and stability of the sugar molecule, making it a valuable tool in glycosylation reactions. The benzyl group at the 3 position and the isopropylidene group across the 1 and 2 positions are crucial for preventing unwanted side reactions during chemical syntheses, allowing researchers to explore and control the formation of glycosidic bonds with high specificity and efficiency. This furanose form of glucose is particularly significant in the synthesis of complex oligosaccharides and glycoconjugates, providing insights into how sugars interact in biological systems and the synthetic pathways that can be used to mimic these interactions. In research, 3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose is used to study the mechanisms of enzyme catalysis involving carbohydrate-processing enzymes such as glycosidases and glycosyltransferases. By modifying the structure of glucose, scientists can gain a deeper understanding of enzymatic specificity and kinetics, which is fundamental for advancing glycoscience. These applications are purely scientific, focusing on enhancing our knowledge of carbohydrate chemistry and developing new synthetic strategies.