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

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2021 Jun 22

PMID 34156858

Citations 2

Authors

Ana M Gomez

Clara Uriel

Ainhoa Oliden-Sanchez

Jorge Banuelos

Inmaculada Garcia-Moreno

J Cristobal Lopez

Affiliations

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Abstract

Novel, linker-free, BODIPY-carbohydrate derivatives containing sugar residues at positions C2 and C6 are efficiently obtained by, hitherto unreported, Ferrier-type -glycosylation of 8-aryl-1,3,5,7-tetramethyl BODIPYs with commercially available tri--acetyl-d-glucal followed by saponification. This transformation, which involves the electrophilic aromatic substitution (SAr) 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.

Citing Articles

Access to BODIPY -Glycosides as Linker-Free Nonsymmetrical BODIPY-Carbohydrate Conjugates.

Uriel C, Grenier D, Herranz F, Casado N, Banuelos J, Rebollar E J Org Chem. 2024; 89(6):4042-4055.

PMID: 38438277 PMC: 10949249. DOI: 10.1021/acs.joc.3c02907.

4,4'-Dicyano- versus 4,4'-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications.

Ventura J, Uriel C, Gomez A, Avellanal-Zaballa E, Banuelos J, Rebollar E Org Lett. 2023; 25(15):2588-2593.

PMID: 37026858 PMC: 10127263. DOI: 10.1021/acs.orglett.3c00476.

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