1138026-23-9Relevant articles and documents
Synthesis of S-glycosyl primary sulfonamides
Lopez, Marie,Drillaud, Nicolas,Bornaghi, Laurent F.,Poulsen, Sally-Ann
experimental part, p. 2811 - 2816 (2009/09/08)
The 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 monoand disaccharide derivatives were synthesized using this new methodology