Synthesis of a new glycosyl-acceptor derivative of normuramic acid lactam and its use for the preparation of a spacer-armed disaccharide structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan

Abstract

A new, highly reactive spacer-armed glycosyl-acceptor derivative of normuramic acid latam was synthesised using an optimized synthetic scheme. The scheme allowed the complete suppression of the side intramolecular N-alkylation reaction occurring during the preparation of this substance using a method based on intramolecular 3-O-alkylation. It was shown that intramolecular N-alkylation in the 3-chloropropylglycoside derivative of normuramic acid lactam led to the formation of an unusual tetracyclic derivative. The reaction of the synthesized reactive glycosyl-acceptor 4-hydroxy derivative with the lowre active 2-methyl-glucopyrano-[2,1-d]-2-oxazoline glycosyl-donor resulted in a spacer-armed disaccharide derivative of normuramic acid lactam structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan.