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

• DOI: 10.1002/ajoc.201800345
• Publication Date: 2018-07-27T06:08:53Z
• Authors: Sujit Manmode; Moeko Kato; Tsuyoshi Ichiyanagi; Toshiki Nokami; Toshiyuki Itoh
• Keywords: Glycosidic bond; Reactivity; Anodic oxidation

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