title: Electron-transfer reduction of 1-deoxy-1-nitroalditols to glycamines with ferrous hydroxide.
abstract: Treatment of eight different 1-deoxy-1-nitroalditols with freshly prepared ferrous hydroxide at ambient temperature provides the corresponding glycamines that were isolated in 81-94% yields as salts with TFA. Under such modified reaction conditions, the retro-Henry reaction of the starting compounds is significantly suppressed due to the amphoteric character of the reducing agent in water. Lower, 58-75% yields were obtained by the classical process with ferrous sulfate in aqueous ammonia and employing an improved purification procedure for the product glycamines by irreversible capture of sulfate ions with barium carbonate.
authors.affiliation: Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia.
authors.forename: Božena
authors.initials: B
authors.lastname: Pribulová
authors.forename: Mária
authors.initials: M
authors.lastname: Petrušová
authors.forename: Hana
authors.initials: H
authors.lastname: Smrtičová
authors.forename: Ladislav
authors.initials: L
authors.lastname: Petruš
mesh_terms: D004579:Electron Transport; D005290:Ferric Compounds / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: D005290:Ferric Compounds; D005296:Ferrous Compounds; D013402:Sugar Alcohols; C021024:ferric hydroxide; C020748:ferrous sulfate