A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation | Zendy

Ana M. Gómez | Zendy; Clara Uriel | Zendy; Ainhoa OlidenSánchez | Zendy; Jorge Bañuelos | Zendy; Inmaculada GarcíaMoreno | Zendy; J. Cristóbal López | Zendy

Open Access

A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation

Author(s) -

Ana M. Gómez,

Clara Uriel,

Ainhoa OlidenSánchez,

Jorge Bañuelos,

Inmaculada GarcíaMoreno,

J. Cristóbal López

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00413

Subject(s) - chemistry , bodipy , glycosylation , oxocarbenium , carbohydrate , allylic rearrangement , linker , combinatorial chemistry , organic chemistry , fluorescence , biochemistry , catalysis , nucleophile , physics , quantum mechanics , computer science , operating system

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- O -acetyl-d-glucal followed by saponification. This transformation, which involves the electrophilic aromatic substitution (S E Ar) 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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