A concise route to water-soluble 2,6-disubstituted BODIPY-carbohydrate fluorophores by direct Ferrier-type C‑Glycosylation

Abstract

[EN] Novel, linker-free, BODIPY-carbohydrate derivatives containing sugar residues at positions C2 and C6 are efficiently obtained by, hitherto unreported, Ferrier-type C-glycosylation of 8- aryl-1,3,5,7-tetramethyl BODIPYs with commercially available tri-Oacetyl- D-glucal followed by saponification. This transformation, which involves the electrophilic aromatic substitution (SEAr) of the dipyrrin framework with an allylic oxocarbenium ion, provides easy access to BODIPY-carbohydrate hybrids with excellent photophysical properties and a weaker tendency to aggregate in concentrated water solutions.