Selective synthesis and ester cleavage property of 3A,2B-anhydro-3B-deoxy-3B-thio-β-cyclodextrin

The title compound was synthesized by the conversion of 2A,3A-alloepoxy-β-cyclodextrin to the 2A,3A-mannoepithio derivative with thiourea and subsequent ring-opening by intramolecular nucleophilic substitution. Its thiol group and the distorted cavity demonstrated good synergetic effect in promoting the cleavage of m-nitrophenyl acetate but did not cooperate with each other toward the p-isomer.