4-O-Acetyl-2,5-anhydro-1,3-O-isopropylidene-6-[bis(2-cyanoethyl)phosphoryl]-D-glucitol (CAS 1041021-85-5)

4-O-Acetyl-2,5-anhydro-1,3-O-isopropylidene-6-[bis(2-cyanoethyl)phosphoryl]-D-glucitol, commonly referred to as 4-APCIG, is a synthetic compound used extensively in the field of organic chemistry and chemical biology. Its chemical structure features a glucitol backbone substituted with acetyl and bis(2-cyanoethyl)phosphoryl groups. One of the primary applications of 4-APCIG lies in its role as a versatile protecting group in carbohydrate chemistry. The acetyl and isopropylidene moieties serve to protect hydroxyl groups, enabling selective functionalization of other hydroxyls within carbohydrates. This property makes 4-APCIG valuable in the synthesis of complex carbohydrates and glycoconjugates, where precise control over regioselectivity and stereochemistry is crucial. Additionally, the bis(2-cyanoethyl)phosphoryl groups can act as leaving groups in glycosylation reactions, facilitating the formation of glycosidic bonds. Furthermore, 4-APCIG has been utilized in the preparation of glycosyl phosphates, which serve as glycosyl donors in glycosylation reactions catalyzed by glycosyltransferases. These enzymes are essential in the biosynthesis of oligosaccharides and glycoconjugates in living organisms. Beyond its utility in carbohydrate chemistry, 4-APCIG has found applications in the synthesis of phosphorus-containing compounds and in the development of novel chemical probes for studying biological processes involving carbohydrates. Overall, 4-O-Acetyl-2,5-anhydro-1,3-O-isopropylidene-6-[bis(2-cyanoethyl)phosphoryl]-D-glucitol is a valuable tool in chemical synthesis and chemical biology research, facilitating the construction of complex carbohydrates and enabling investigations into their biological roles and interactions.