title: Synthesis of sulfonamide-bridged glycomimetics.
abstract: A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1↔1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.
authors.affiliation: Eskitis Institute, Griffith University, Nathan Campus, Queensland, 4111, Australia.
authors.forename: Marie
authors.initials: M
authors.lastname: Lopez
authors.forename: Laurent F
authors.initials: LF
authors.lastname: Bornaghi
authors.forename: Hugues
authors.initials: H
authors.lastname: Driguez
authors.forename: Sally-Ann
authors.initials: SA
authors.lastname: Poulsen
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D006027:Glycosides; D013449:Sulfonamides