Control of the regioselectivity for new fluorinated amphiphilic cyclodextrins: synthesis of di- and tetra(6-deoxy-6-alkylthio)- and 6-(perfluoroalkypropanethio)-alpha-cyclodextrin derivatives

The Journal of Organic Chemistry
Bernard Bertino-GheraHélène Parrot-Lopez

Abstract

Twelve new di- and tetraderivatized alpha-cyclodextrin molecules having either alkylthio and perfluoroalkylpropanethio functions at the primary face have been synthesized by using the procedure of Sinay for di-O-debenzylation of perbenzylated alpha-cyclodextrins. A new strategy of protection/deprotection has been developed for introducing the lipophilic chains. The coupling reaction involves the reaction between the appropriate alpha-cyclodextin derivative, regioselectively modified at C-6 positions by a good leaving group (O-mesityl for disubstituted or iodine for tetrasubstituted derivatives), with the thioalkyl or the thioperfluoroakylpropane chains. These nucleophilic reagents are obtained from the in situ basic hydrolysis of the alkylisothiouronium bromides or perfluoalkylropropane and the isothiouronium iodides. These multistep reactions give the desired amphiphilic alpha-cyclodextrins in good overall yields of 33% to 58%.

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Citations

May 18, 2010·Chemical Communications : Chem Comm·Maria M Becker, Bart Jan Ravoo
Oct 18, 2012·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Florent PerretHélène Parrot-Lopez
Nov 17, 2012·International Journal of Pharmaceutics·Florent PerretMarc Le Borgne
Jan 27, 2018·Pharmaceuticals·Abdelhamid NacereddineMarc Le Borgne
Jan 18, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Anthony PrandinaFlorent Perret

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