Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective su...

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Detalles Bibliográficos
Autores: Traverssi, Miqueas Gabriel, Peñeñory, Alicia Beatriz, Varela, Oscar Jose, Colomer, Juan Pablo
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/180991
Acceso en línea:http://hdl.handle.net/11336/180991
Access Level:acceso abierto
Palabra clave:CARBOHYDRATES
SULFOXIDES
PHOTOOXIDATION
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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repository_id_str
spelling Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditionsTraverssi, Miqueas GabrielPeñeñory, Alicia BeatrizVarela, Oscar JoseColomer, Juan PabloCARBOHYDRATESSULFOXIDESPHOTOOXIDATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.Fil: Traverssi, Miqueas Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Colomer, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaRoyal Society of Chemistry2021-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/180991Traverssi, Miqueas Gabriel; Peñeñory, Alicia Beatriz; Varela, Oscar Jose; Colomer, Juan Pablo; Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions; Royal Society of Chemistry; RSC Advances; 11; 16; 2-2021; 9262-92732046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/d0ra09534finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:20:30Zoai:ri.conicet.gov.ar:11336/180991instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 14:20:30.397CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
title Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
spellingShingle Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
Traverssi, Miqueas Gabriel
CARBOHYDRATES
SULFOXIDES
PHOTOOXIDATION
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
title_full Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
title_fullStr Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
title_full_unstemmed Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
title_sort Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
dc.creator.none.fl_str_mv Traverssi, Miqueas Gabriel
Peñeñory, Alicia Beatriz
Varela, Oscar Jose
Colomer, Juan Pablo
author Traverssi, Miqueas Gabriel
author_facet Traverssi, Miqueas Gabriel
Peñeñory, Alicia Beatriz
Varela, Oscar Jose
Colomer, Juan Pablo
author_role author
author2 Peñeñory, Alicia Beatriz
Varela, Oscar Jose
Colomer, Juan Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv CARBOHYDRATES
SULFOXIDES
PHOTOOXIDATION
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic CARBOHYDRATES
SULFOXIDES
PHOTOOXIDATION
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.
publishDate 2021
dc.date.none.fl_str_mv 2021-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/180991
Traverssi, Miqueas Gabriel; Peñeñory, Alicia Beatriz; Varela, Oscar Jose; Colomer, Juan Pablo; Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions; Royal Society of Chemistry; RSC Advances; 11; 16; 2-2021; 9262-9273
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/180991
identifier_str_mv Traverssi, Miqueas Gabriel; Peñeñory, Alicia Beatriz; Varela, Oscar Jose; Colomer, Juan Pablo; Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions; Royal Society of Chemistry; RSC Advances; 11; 16; 2-2021; 9262-9273
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/d0ra09534f
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1799196253720936448
score 15,811543

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