The Reactivity of 1- [formula omitted]-α- D-glucopyranosyl- D-fructose (trehalulose) in pyridinium poly(hydrogen fluoride) or anhydrous HF. New D-glucose D-fructose mixed dianhydrides

Abstract

Trehalulose undergoes intramolecular glycosylation when dissolved in pyridinium poly(hydrogen fluoride) or liquid HF, yielding a mixture of two α- D-glucopyranose β- D-fructose 1, 1′:2,2′-dianhydrides. The reaction can be directed to the kinetic fructofuranose or to the thermodynamic fructopyranose derivative by acting on the protonation conditions. The mechanism likely involves reactive cyclic oxocarbenium ions.