Automated Electrochemical Assembly of the β‐(1,3)‐β‐(1,6)‐Glucan Hexasaccharide Using Thioglucoside Building Blocks

Abstract

AbstractThis study deals with the design, synthesis, and rational optimization of carbohydrate building blocks of glucosides for automated electrochemical assembly of β‐glucans. Oxidation potentials of building blocks with various types of protecting groups of hydroxyl groups were measured to estimate their reactivity under anodic oxidation conditions. Building blocks for both β‐1,3‐ and β‐1,6‐glycosidic linkages were optimized by an automated electrochemical assembly of disaccharides and trisaccharides. Several synthetic attempts were also made for the synthesis of the hexasaccharide repeating unit in a macrocyclic β‐glucan tridecasaccharide.