BROMINE OXIDATION OF 1,2-O-ISOPROPYLIDINE-α-D-GLUCOFURANOSE AND SUCROSE

Article abstract of DOI:10.1016/0008-6215(80)90006-3

Sucrose and 1,2-O-isopropylidene-α-D-glucofuranose (1) were oxidised with bromine in aqueous solution at pH 7 and room temperature.The resulting keto derivatives were converted into their more-stable O-methyloximes, which were characterised by spectroscopic and chromatographic methods.Oxidation of 1 occured at C-3 and C-5, with a preference for C-5.In the sucrose derivatives isolated after oxidation, those having a keto group in the glucopyranosyl moiety preponderated.The axial fructofuranosyl aglycon protects position 3 in the glucopyranosyl group and oxidation occurs only at C-2 and C-4.Small amounts of sucrose oxidised at C-3 in the fructofuranosyl moiety were also found.