Improved access to 2-O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis

A comparative study of reaction conditions was performed for the synthesis of a 2-O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me2SO and benzyl bromide. The methodology was extended to the preparation of various 2I-O-iodobenzyl and 2I-O-carboxymethylbenzyl derivatives of β-CD including a 3-carboxymethyl-4-iodobenzyl derivative of interest as precursor of an enzyme mimic to degrade the organophosphoryl ester diethyl 4-nitrophenyl phosphate (paraoxon).