A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
2021; American Chemical Society; Volume: 86; Issue: 13 Linguagem: Inglês
10.1021/acs.joc.1c00413
ISSN1520-6904
AutoresAna M. Gómez, Clara Uriel, Ainhoa Oliden‐Sánchez, Jorge Bañuelos, Inmaculada García‐Moreno, J. Cristóbal López,
Tópico(s)Molecular Sensors and Ion Detection
ResumoNovel, 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-O-acetyl-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.
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