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

• Published in: Carbohydrate research Vol. 341; no. 7; pp. 935 - 940
• Main Authors: Masurier, Nicolas, Estour, François, Lefèvre, Bertrand, Brasme, Bernard, Masson, Patrick, Lafont, Olivier
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.05.2006; Elsevier
• Subjects: Benzyl ethers; beta-Cyclodextrins - chemistry; Biochemistry & Molecular Biology; Catalysis; Catalysts; Chemical Sciences; Chemistry; Chemistry, Applied; Chemistry, Organic; Enzyme mimics; Esters - metabolism; Ethanol - analogs & derivatives; Ethanol - chemistry; Ethers - chemical synthesis; Ethers - chemistry; Hydrolysis; Life Sciences; Life Sciences & Biomedicine; Organophosphoryl esters; Paraoxon - metabolism; Physical Sciences; Science & Technology; β-Cyclodextrin monosubstitution; β-Cyclodextrin monosubstitution; Catalysts; Benzyl ethers; Enzyme mimics; Organophosphoryl esters; organophosphoryl esters; benzyl ethers; REACTIVE PHOSPHATES; ALKYLATION; CYCLOMALTOHEPTAOSE; COMPLEXES; CLEAVAGE; REGIOSELECTIVITY; catalysts; beta-cyclodextrin monosubstitution; DERIVATIVES; enzyme mimics; ORTHO-IODOSOBENZOATE
• ISSN: 0008-6215; 1873-426X; 0008-6215
• DOI: 10.1016/j.carres.2006.02.012

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 Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- 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).