Synthesis of 1,2-O-isopropylidene-3,5-O-propylidene-α–d-glucofuranose as a convenient precursor of both 6-O-alkyl and 6-O-glycidyl-d-glucose amphiphiles

1,2-O-Isopropylidene-3,5-O-propylidene-α-d-glucofuranose (3) was synthesized by conversion of 3-O-allyl-1,2-O-isopropylidene-α-d-glucofuranose (1) into its 3-O-prop-1-enyl isomer (2), followed by rapid acid-catalysed intramolecular acetalation in an aprotic solvent. The diacetal 3 was used as the precursor of 6-O-alkyl and 6-O-glucidyl-d-glucose amphiphiles, which show thermotropic and lyotropic liquid-crystalline properties.