Perfluoroalkylated derivatives of 6-deoxy-6-ethylamino-d-galactose, 1-deoxy-1-methylamino-d-glucitol, and 1-amino-1-deoxy-d-glucitol: syntheses, hemocompatibility, and effect on perfluorocarbon emulsion Original Research Article

N-Polyfluoroalkyl derivatives of 6-deoxy-6-ethylamino-1,2;3,4-di-O-isopropylidene-α-d-galactopyranose (8–10), 1-deoxy-1-methylamino-d-glucitol (13–15), and 1-amino-1-deoxy-d-glucitol (16–18), all possessing perfluoroalkyl segment, were prepared using nucleophilic epoxide ring opening of 2-[(perfluoroalkyl)methyl]oxiranes 1–3. Co-emulsifying properties and hemolytic activity of the new perfluoroalkylated amphiphiles were tested. Both types of the polyol derivatives 8–10 and 13–18 generally displayed good to excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions. Mono-perfluoroalkylated compounds 8–10 and 13–15 displayed high hemolysis, whereas acyclic bis-perfluoroalkylated compounds 16–18 were non-hemolytic even for short perfluorobutyl segment (16). The properties were generally improving with increasing perfluoroalkyl chain length.