Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.
- regioselective protection