title: The iodosulfonamidation of peracetylated glycals revisited: access to 1,2-di-nitrogenated sugars.
abstract: Iodosulfonamidation of peracetylated glycals was investigated using either a combination of N-iodosuccinimide/iodine or iodine chloride as a source of iodonium ion. 1,2-trans- and 1,2-cis-2-deoxy-2-iodo-1-sulfonamido hexoses were, respectively, obtained depending on the reagent system used. Both series of isomers were successfully converted to 1,2-di-nitrogenated compounds, for example, 1-azido-1,2-dideoxy-2-sulfonamido sugars, which are useful intermediates for the synthesis of N-linked glycoproteins or glycoconjugates.
authors.affiliation: Laboratoire des Glucides, UMR CNRS 6219, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
authors.forename: François-Moana
authors.initials: FM
authors.lastname: Gautier
authors.forename: Florence
authors.initials: F
authors.lastname: Djedaïni-Pilard
authors.forename: Cyrille
authors.initials: C
authors.lastname: Grandjean
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000606:Amino Sugars / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000085:Acetates; D000606:Amino Sugars; D001386:Azides; D002241:Carbohydrates; D006027:Glycosides; D013449:Sulfonamides; C474740:iodosulfonamide