Carbohydrates and BODIPYs: access to bioconjugatable and water-soluble BODIPYs

Abstract Fluorescent difluoroboron dipyrromethenes (BODIPYs), have been accessed in a one-pot synthetic operation from phthalides and pyrroles, a process that involves O -ethylation of phthalides with Meerwein’s reagent (Et 3 OBF 4 ) and reaction of the ensuing tetrafluoroborate salts with pyrrole, followed by treatment with BF 3 · OEt 2 . These derivatives are endowed with a ortho -hydroxymethyl 8- C -aryl group for further derivatization and/or conjugation to, among others, carbohydrates. The new conjugate derivatives benefit from the optimal characteristics of BODIPYs as fluorescent dyes, including in some instances water-solubility (in the case of conjugation to unprotected carbohydrates). The different kinds of BODIPY-carbohydrate derivatives are compounds of potential interest for biological studies.