Show simple item record

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

dc.contributor.authorGómez López, Ana María
dc.contributor.authorUriel, Clara
dc.contributor.authorOliden Sánchez, Ainhoa
dc.contributor.authorBañuelos Prieto, Jorge ORCID
dc.contributor.authorGarcía Moreno, Inmaculada
dc.contributor.authorLópez Pérez, José Cristóbal
dc.date.accessioned2021-09-02T10:07:31Z
dc.date.available2021-09-02T10:07:31Z
dc.date.issued2021-06-22
dc.identifier.citationThe Journal of Organic Chemistry 86 : 9181−9188 (2021)es_ES
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/10810/52896
dc.description.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.es_ES
dc.description.sponsorshipThe authors gratefully acknowledge the Spanish Ministerio de Ciencia e Innovación for financial support (Projects RTI2018- 094862-B-100, MAT2017-83856-C3-1-P and -3-P, and PiD2020-114755GB-C31 and -C33) and the Gobierno Vasco (Project IT912-16) for financial support. The authors are indebted to Mr. Diego Pozas and Ms. Marina Rodríguez (IQOG-CSIC) for skillful technical support. A.O.-S. thanks UPV/EHU for her predoctoral fellowship.es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/RTI2018-094862-B-100es_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/MAT2017-83856-C3-1-Pes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/MAT2017-83856-C3-3-Pes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/PiD2020-114755GB-C31es_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/PiD2020-114755GB-C33es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.titleA concise route to water-soluble 2,6-disubstituted BODIPY-carbohydrate fluorophores by direct Ferrier-type C‑Glycosylationes_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2021 The Authors. Published by American Chemical Society. https://creativecommons.org/licenses/by/4.0/es_ES
dc.rights.holderAtribución 3.0 España*
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.1c00413es_ES
dc.identifier.doi10.1021/acs.joc.1c00413
dc.departamentoesQuímica físicaes_ES
dc.departamentoeuKimika fisikoaes_ES


Files in this item

Thumbnail
Name:
acs.joc.1c00413.pdf
Size:
1.129Mb
Format:
PDF
Description:
Artículo principal
View/Open
Thumbnail
Name:
license_rdf
Size:
914bytes
Format:
application/rdf+xml
View/Open

This item appears in the following Collection(s)

Show simple item record

© 2021 The Authors. Published by American Chemical Society. https://creativecommons.org/licenses/by/4.0/
Except where otherwise noted, this item's license is described as © 2021 The Authors. Published by American Chemical Society. https://creativecommons.org/licenses/by/4.0/