Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

Abstract

The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.

Keywords

• automated synthesis
• electrochemical oxidation
• glycosylation
• glucosamine
• total synthesis