Pathways in the synthesis of functionalized glycolipids for liposomal preparations

Abstract

We describe in this paper the synthesis of two glycolipids containing a mannosyl residue functionalized with malonic acid and azide groups at the C6 position. Two synthetic routes have been successfully implemented: the first one involves Schmidt's glycosylation procedure using functionalized carbohydrates, whereas the second one involves nucleophilic substitutions in the C6 position of an iodinated intermediate obtained using Koenigs-Knorr reaction. A comparative discussion of reactions and yields is realized. The two glycolipids served as material for the preparation of liposomes.

Keywords: Azide; Glycolipids; Glycosylation; Liposomes; Malonic acid; Mannose.