Ethyl 2,3-Di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside S-Oxide (CAS 188357-34-8)

Ethyl 2,3-Di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside S-Oxide is a highly specialized thio-sugar derivative extensively utilized in carbohydrate chemistry and organic synthesis research. This chemical is particularly notable for its sulfur-containing substituent, which replaces a traditional oxygen atom in the sugar ring, thereby altering its chemical reactivity and stability. The thioether linkage (S-oxide) at the 1-position introduces unique electronic and steric properties, making it an invaluable tool for studying glycosylation reactions under various conditions. The benzyl and benzylidene protective groups on other hydroxyl groups of the sugar enhance its stability and make it resistant to unwanted side reactions, facilitating its use in the selective formation of glycosidic bonds. In research, this compound is often used to probe the mechanistic aspects of glycosyl transfer reactions, especially how thioethers can influence glycosylation compared to their oxygen counterparts. It serves as a critical model for synthesizing glycosidic bonds in a controlled manner, allowing chemists to manipulate the reaction conditions to favor specific outcomes. This is pivotal for the development of synthetic strategies that mimic natural glycosylation processes, offering insights into more efficient synthesis of complex carbohydrates and glycoconjugates.