Synthesis of Novel Carbohydrate-diol Derivatives via Stereoselective Anomeric Deacetylation and Sulfonation Reactions

Abstract

Carbohydrates play vital roles in both biological systems and materials science. In this study, an efficient synthetic route is presented for the preparation of novel carbohydrate– diol–sulfonate conjugates derived from sugars such as glucose and fructose. Through a sequence involving peracetylation, selective anomeric deacetylation using tin oxide, and subsequent sulfonation, reactive glycosyl donors were successfully synthesized. These compounds hold considerable potential for applications in advanced drug delivery systems. The study employs materials sourced from Sigma-Aldrich to develop an efficient synthetic route for novel carbohydrate–diol conjugates. Through a sequential process involving peracetylation, selective anomeric deacetylation, and diol coupling, glucose, fructose, lactose, mannose, and sucrose are transformed into reactive glycosyl donors through anomeric sulfonation. This synthetic strategy facilitates the construction of advanced molecular architectures with potential applications in carbohydrate- based molecular design. Various saccharides were initially subjected to complete acetylation using acetic anhydride in the presence of sodium acetate as a catalyst. Subsequently, the anomeric protecting group was selectively removed using tin oxide, thereby freeing the anomeric hydroxyl group. The resulting intermediates were then reacted with various diols to generate new derivatives, which were subsequently sulfonated at the anomeric position using Methanesulfonyl Chloride (MsCl). The synthesized compounds were finally characterized and confirmed by spectroscopic analysis. Saccharides undergo a sequence of acetylation, selective deacetylation, diol coupling, and anomeric sulfonation to yield novel carbohydrate–diol conjugates, which are confirmed through spectroscopic analysis. This synthetic approach efficiently generates reactive glycosyl donors, providing valuable building blocks for constructing advanced molecular architectures. This research presents a streamlined synthetic route for preparing carbohydrate–diol– sulfonate derivatives from readily available sugars through a sequence of selective acetylation, deacetylation, and sulfonation steps. The developed method enables the generation of structurally tunable compounds with enhanced reactivity as glycosyl donors, demonstrating promising potential for the development of glycoconjugate biomaterials and advanced drug delivery applications.