Synthesis of double-tailed (perfluoroalkyl)alkyl phosphosugars: new components for drug-carrying and -targeting systems

摘要: Abstract Double-tailed d -glycose 3- and 6-[sodium (perfluoroalkyl)alkyl phosphates] were synthesized via the hydrogen phosphonate approach. Stable double-tailed hydrogenphosphonates, prepared from (perfluoroalkyl)alkanols PCl 3 -imidazole, reacted with 1,2:3,4-di- O -isopropylidene-α- -galactopyranose or 1,2:5,6 -di- -glucofuranose in presence of Me CCOCl as condensing agent to give, after oxidation aqueous iodine, corresponding -protected glycose phosphate diesters. -Deisopropylidenation latter by trifluoroacetic acid afforded target compound 70% yield, based on protected glycosides. Condensation 1,2,3,4-tetra- -acetyl-β- -glucopyranose -mannopyranose hydrogenphosphonates 10-eicosyl hydrogenphosphonate, coupling steps described above, per- -acetylglycose phosphodiesters. -Deacetylation MeONa-MeOH was achieved 65% yield sugar. All compounds characterized 19 F, 1 H, 13 C, 31 P NMR data. Preliminary biocompatibility assays indicate a reduction hemolytic activity when fluorinated chains are present maximum tolerated doses ca. 125 mg/kg body weight mice.