Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals

Autores
Díaz, Gisela; Ponzinibbio, Agustín; Bravo, Rodolfo Daniel
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.
Fil: Díaz, Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Ponzinibbio, Agustín. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Bravo, Rodolfo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Materia
Wittig Reaction
Exo-Glycals
Hydrogenation
Palladium Catalyst
C-Glycosides
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/32423
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycalsDíaz, GiselaPonzinibbio, AgustínBravo, Rodolfo DanielWittig ReactionExo-GlycalsHydrogenationPalladium CatalystC-Glycosideshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.Fil: Díaz, Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Ponzinibbio, Agustín. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Bravo, Rodolfo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaElsevier2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/32423Díaz, Gisela; Ponzinibbio, Agustín; Bravo, Rodolfo Daniel; Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals; Elsevier; Carbohydrate Research; 393; 4-2014; 23-250008-6215CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2014.04.009info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S000862151400161Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T10:48:47Zoai:ri.conicet.gov.ar:11336/32423instacron: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:34982025-11-05 10:48:47.638CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
title Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
spellingShingle Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
Díaz, Gisela
Wittig Reaction
Exo-Glycals
Hydrogenation
Palladium Catalyst
C-Glycosides
title_short Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
title_full Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
title_fullStr Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
title_full_unstemmed Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
title_sort Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
dc.creator.none.fl_str_mv Díaz, Gisela
Ponzinibbio, Agustín
Bravo, Rodolfo Daniel
author Díaz, Gisela
author_facet Díaz, Gisela
Ponzinibbio, Agustín
Bravo, Rodolfo Daniel
author_role author
author2 Ponzinibbio, Agustín
Bravo, Rodolfo Daniel
author2_role author
author
dc.subject.none.fl_str_mv Wittig Reaction
Exo-Glycals
Hydrogenation
Palladium Catalyst
C-Glycosides
topic Wittig Reaction
Exo-Glycals
Hydrogenation
Palladium Catalyst
C-Glycosides
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.
Fil: Díaz, Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Ponzinibbio, Agustín. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Bravo, Rodolfo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
description Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/32423
Díaz, Gisela; Ponzinibbio, Agustín; Bravo, Rodolfo Daniel; Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals; Elsevier; Carbohydrate Research; 393; 4-2014; 23-25
0008-6215
CONICET Digital
CONICET
url http://hdl.handle.net/11336/32423
identifier_str_mv Díaz, Gisela; Ponzinibbio, Agustín; Bravo, Rodolfo Daniel; Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals; Elsevier; Carbohydrate Research; 393; 4-2014; 23-25
0008-6215
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2014.04.009
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S000862151400161X
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
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
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score 13.087074

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