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

Carbohydrate Research
Nicolas MasurierOlivier Lafont

Abstract

A comparative study of reaction conditions was performed for the synthesis of a 2-O-monobenzyl ether of cyclomaltoheptaose (beta-CD). Optimal conditions involved sodium ethoxide in Me(2)SO and benzyl bromide. The methodology was extended to the preparation of various 2(I)-O-iodobenzyl and 2(I)-O-carboxymethylbenzyl derivatives of beta-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).

References

Feb 19, 2002·Chemical Reviews·Abdul Rauf KhanValerian T. D'Souza
Apr 2, 2002·The Journal of Organic Chemistry·Vadims Dvornikovs, David B Smithrud

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Citations

Nov 3, 2010·Toxicology Letters·Susanne MüllerGeorg Reiter
Mar 14, 2009·Chemical Communications : Chem Comm·Nicolas MasurierFrançois Estour
Apr 7, 2017·Beilstein Journal of Organic Chemistry·Sophie LetortFrançois Estour
Mar 16, 2016·Beilstein Journal of Organic Chemistry·Sophie LetortFrançois Estour
Dec 17, 2010·Beilstein Journal of Organic Chemistry·Ivan SnajdrMartin Kotora
Mar 5, 2011·Organic & Biomolecular Chemistry·Romain Le ProvostFrançois Estour

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