1,2-O-Cyclohexylidene-3-O-methyl-α-D-glucofuranose (CAS 13322-87-7)

1,2-O-Cyclohexylidene-3-O-methyl-α-D-glucofuranose is a derivative of α-D-glucofuranose where the hydroxyl groups at positions 1 and 2 are protected by a cyclohexylidene group, and the hydroxyl group at position 3 is methylated. This chemical modification enhances the stability and solubility of the molecule in organic solvents, making it a valuable intermediate in synthetic carbohydrate chemistry. The cyclohexylidene group acts as a protective group that can be selectively removed under acidic conditions, allowing for stepwise synthesis of complex carbohydrates. In research, 1,2-O-Cyclohexylidene-3-O-methyl-α-D-glucofuranose is used to study glycosylation mechanisms and the formation of glycosidic bonds. Its stability allows it to be employed in the synthesis of oligosaccharides and glycoconjugates, which are crucial for investigating carbohydrate-protein interactions, cell recognition processes, and signal transduction pathways. This compound is also used as a building block in the development of glycomimetics, which mimic natural glycans and are used to study their role in biological systems. Additionally, 1,2-O-Cyclohexylidene-3-O-methyl-α-D-glucofuranose is utilized in the synthesis of nucleotide sugars and other sugar derivatives, aiding in the exploration of enzyme specificity and kinetics in carbohydrate metabolism. Its role in these synthetic applications underscores its importance in advancing the understanding of carbohydrate chemistry and the development of novel biochemical tools.