Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

Abstract

In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.