Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor

Autores
Della Felice, Franco; Rúveda, Edmundo; Stortz, Carlos Arturo; Colombo, María Inés
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An assessment of the relative O-3/O-4 reactivities of both -methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a -glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3.
Fil: Della Felice, Franco. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Rúveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Stortz, Carlos Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Colombo, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Glycosyl Donor
Superarmed Donor
Regioselectivity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/2135
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donorDella Felice, FrancoRúveda, EdmundoStortz, Carlos ArturoColombo, María InésGlycosyl DonorSuperarmed DonorRegioselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An assessment of the relative O-3/O-4 reactivities of both -methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a -glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3.Fil: Della Felice, Franco. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Rúveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Stortz, Carlos Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Colombo, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaElsevier2013-10-18info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2135Della Felice, Franco; Rúveda, Edmundo; Stortz, Carlos Arturo; Colombo, María Inés; Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor; Elsevier; Carbohydrate Research; 380; 18-10-2013; 167-1730008-6215enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621513002851info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2013.08.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:54:49Zoai:ri.conicet.gov.ar:11336/2135instacron: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:34982025-09-03 09:54:49.303CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
title Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
spellingShingle Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
Della Felice, Franco
Glycosyl Donor
Superarmed Donor
Regioselectivity
title_short Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
title_full Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
title_fullStr Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
title_full_unstemmed Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
title_sort Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
dc.creator.none.fl_str_mv Della Felice, Franco
Rúveda, Edmundo
Stortz, Carlos Arturo
Colombo, María Inés
author Della Felice, Franco
author_facet Della Felice, Franco
Rúveda, Edmundo
Stortz, Carlos Arturo
Colombo, María Inés
author_role author
author2 Rúveda, Edmundo
Stortz, Carlos Arturo
Colombo, María Inés
author2_role author
author
author
dc.subject.none.fl_str_mv Glycosyl Donor
Superarmed Donor
Regioselectivity
topic Glycosyl Donor
Superarmed Donor
Regioselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An assessment of the relative O-3/O-4 reactivities of both -methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a -glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3.
Fil: Della Felice, Franco. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Rúveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Stortz, Carlos Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Colombo, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description An assessment of the relative O-3/O-4 reactivities of both -methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a -glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3.
publishDate 2013
dc.date.none.fl_str_mv 2013-10-18
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/11336/2135
Della Felice, Franco; Rúveda, Edmundo; Stortz, Carlos Arturo; Colombo, María Inés; Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor; Elsevier; Carbohydrate Research; 380; 18-10-2013; 167-173
0008-6215
url http://hdl.handle.net/11336/2135
identifier_str_mv Della Felice, Franco; Rúveda, Edmundo; Stortz, Carlos Arturo; Colombo, María Inés; Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor; Elsevier; Carbohydrate Research; 380; 18-10-2013; 167-173
0008-6215
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621513002851
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2013.08.002
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv 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 13.13397

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