jo9000367_si_001.pdf (545.28 kB)
Synthesis of S-Glycosyl Primary Sulfonamides
journal contribution
posted on 2009-04-03, 00:00 authored by Marie Lopez, Nicolas Drillaud, Laurent F. Bornaghi, Sally-Ann PoulsenThe synthesis of S-glycosyl sulfonamides wherein the primary sulfonamide functional group (−SO2NH2) is directly attached to the anomeric position of a carbohydrate moiety is reported. Our general approach consists of first introducing a thioacetate group at the anomeric center of a per-O-acetylated sugar derivative. From this follows formation of a glycosyl sulfenamide (sugar-SNR2), oxidation of the sulfenamide to give a glycosyl N-protected sulfonamide (sugar-SO2NR2), and removal of the sulfonamide protecting (R) group to yield a primary sulfonamide at the anomeric center (sugar-SO2NH2). A variety of mono- and disaccharide derivatives were synthesized using this new methodology.