4,6-O-Ethylidene-α-D-glucose (CAS 13224-99-2)

4,6-O-Ethylidene-α-D-glucose is a derivative of glucose where an ethylidene group is introduced, bridging the 4 and 6 positions of the glucose molecule. This modification stabilizes the glucose structure, altering its reactivity and solubility, making it a valuable compound in carbohydrate chemistry. This derivative is extensively used in the synthesis of glycosyl donors and acceptors, facilitating the formation of glycosidic bonds in the preparation of complex oligosaccharides and glycoconjugates. The ethylidene group acts as a protecting group, which can be selectively removed under mild acidic conditions, allowing for precise control in multi-step synthesis pathways. In research, 4,6-O-Ethylidene-α-D-glucose is employed to study the stereoselectivity and mechanisms of glycosylation reactions. Its unique structure helps in probing the catalytic activity of glycosyltransferases and glycosidases, providing insights into the enzymatic processes involved in carbohydrate biosynthesis and metabolism. Additionally, this compound is instrumental in developing new synthetic methodologies for creating glycosidic linkages with high specificity and yield. It is also used in the synthesis of glycomimetics, which are designed to mimic natural glycans and study their interactions with proteins and other biomolecules. The application of 4,6-O-Ethylidene-α-D-glucose in these areas significantly advances our understanding of carbohydrate chemistry and its implications in biological systems.