Reactivity of melezitose and raffinose under Mitsunobu reaction conditions

The reactivity of melezitose and raffinose under Mitsunobu conditions was studied within the scope of the use of trisaccharides for the synthesis of fatty acid esters. Melezitose led to esters with preferential substitution at primary positions following the order of reactivity 6″ > 6 > 6′. Raffinose proved to be very reluctant toward ester formation in these conditions, leading mainly to the new 3″,6″-anhydroraffinose.