Improved access to 2-O-monobenzyl ethers of beta-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 (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).
Masurier
Nicolas
N
UMR 6014 CNRS, Université de Rouen, INSA de Rouen, Laboratoire de Pharmacochimie, U.F.R. de Médecine et de Pharmacie, 22 Boulevard Gambetta, F-76183 Rouen, France.
Estour
François
F
Lefèvre
Bertrand
B
Brasme
Bernard
B
Masson
Patrick
P
Lafont
Olivier
O
D002384:Catalysis; D004952:Esters / Q000378:metabolism*; D000431:Ethanol / Q000031:analogs & derivatives / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D006868:Hydrolysis; D010261:Paraoxon / Q000378:metabolism*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D004952:Esters; D004987:Ethers; D047392:beta-Cyclodextrins; C098088:sodium ethoxide; D000431:Ethanol; C031215:betadex; D010261:Paraoxon