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

[Image: see text] 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 sa...

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Autores principales: Gómez, Ana M., Uriel, Clara, Oliden-Sánchez, Ainhoa, Bañuelos, Jorge, Garcia-Moreno, Inmaculada, López, J. Cristobal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279486/
https://www.ncbi.nlm.nih.gov/pubmed/34156858
http://dx.doi.org/10.1021/acs.joc.1c00413
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author Gómez, Ana M.
Uriel, Clara
Oliden-Sánchez, Ainhoa
Bañuelos, Jorge
Garcia-Moreno, Inmaculada
López, J. Cristobal
author_facet Gómez, Ana M.
Uriel, Clara
Oliden-Sánchez, Ainhoa
Bañuelos, Jorge
Garcia-Moreno, Inmaculada
López, J. Cristobal
author_sort Gómez, Ana M.
collection PubMed
description [Image: see text] 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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spelling pubmed-82794862021-07-15 A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation Gómez, Ana M. Uriel, Clara Oliden-Sánchez, Ainhoa Bañuelos, Jorge Garcia-Moreno, Inmaculada López, J. Cristobal J Org Chem [Image: see text] 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. American Chemical Society 2021-06-22 2021-07-02 /pmc/articles/PMC8279486/ /pubmed/34156858 http://dx.doi.org/10.1021/acs.joc.1c00413 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Gómez, Ana M.
Uriel, Clara
Oliden-Sánchez, Ainhoa
Bañuelos, Jorge
Garcia-Moreno, Inmaculada
López, J. Cristobal
A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title_full A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title_fullStr A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title_full_unstemmed A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title_short A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation
title_sort concise route to water-soluble 2,6-disubstituted bodipy-carbohydrate fluorophores by direct ferrier-type c-glycosylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279486/
https://www.ncbi.nlm.nih.gov/pubmed/34156858
http://dx.doi.org/10.1021/acs.joc.1c00413
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