title: Reactivity of 2-deoxy-2-iodoglycosyl isothiocyanates with O-, S-, and N-nucleophiles. Synthesis of glycopyranoso-fused thiazoles.
abstract: The reactivity of 2-deoxy-2-iodoglycosyl isothiocyanates toward O- and S-nucleophiles gives an easy access to 2-deoxy-2-iodoglycopyranosyl thiocarbamates and dithiocarbamates. Internal nucleophilic displacement of the iodine by the sulfur atom in these compounds allows the preparation of glycopyranoso[1,2-d]-1,3-thiazoles and glycopyranoso[1,2-d]-1,3-thiazolidin-2-one or -2-thione. Reaction with amines or polyamines as N-nucleophiles led directly to 2-aminoglycopyranoso[1,2-d]-1,3-thiazoles without isolation of the intermediate thioureas. Methyl 2-deoxy-2-iodoglycopyranosyl thiocarbamates also allow the synthesis of 2-deoxyglycopyranosyl thiocarbamates or 2-deoxy-2-iodoglycopyranosyl carbamates.
authors.affiliation: Instituto de Biotecnología. Departamento de Química Orgánica, Facultad de Ciencias, Campus Fuentenueva s/n, Universidad de Granada, Granada, E-18071, Spain.
authors.forename: Joaquin
authors.initials: J
authors.lastname: Isac-García
authors.forename: Fernando
authors.initials: F
authors.lastname: Hernández-Mateo
authors.forename: Francisco G
authors.initials: FG
authors.lastname: Calvo-Flores
authors.forename: Francisco
authors.initials: F
authors.lastname: Santoyo-González