title: Synthesis of S-glycosyl primary sulfonamides.
abstract: The synthesis of S-glycosyl sulfonamides wherein the primary sulfonamide functional group (-SO(2)NH(2)) 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-SNR(2)), oxidation of the sulfenamide to give a glycosyl N-protected sulfonamide (sugar-SO(2)NR(2)), and removal of the sulfonamide protecting (R) group to yield a primary sulfonamide at the anomeric center (sugar-SO(2)NH(2)). A variety of mono- and disaccharide derivatives were synthesized using this new methodology.
authors.affiliation: Eskitis Institute, Griffith University, Brisbane, Queensland 4111, Australia.
authors.forename: Marie
authors.initials: M
authors.lastname: Lopez
authors.forename: Nicolas
authors.initials: N
authors.lastname: Drillaud
authors.forename: Laurent F
authors.initials: LF
authors.lastname: Bornaghi
authors.forename: Sally-Ann
authors.initials: SA
authors.lastname: Poulsen