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

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Bibliographic Details
Published in:Carbohydrate research 2006-05, Vol.341 (7), p.935-940
Main Authors: Masurier, Nicolas, Estour, François, Lefèvre, Bertrand, Brasme, Bernard, Masson, Patrick, Lafont, Olivier
Format: Article
Language:English
Subjects:
Benzyl ethers
beta-Cyclodextrins - chemistry
Catalysis
Catalysts
Chemical Sciences
Enzyme mimics
Esters - metabolism
Ethanol - analogs & derivatives
Ethanol - chemistry
Ethers - chemical synthesis
Ethers - chemistry
Hydrolysis
Life Sciences
Organophosphoryl esters
Paraoxon - metabolism
β-Cyclodextrin monosubstitution
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Summary: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).
ISSN:0008-6215
1873-426X
0008-6215
DOI:10.1016/j.carres.2006.02.012