Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles

The fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent cyclization promoted by hypervalent iodine provide an excellent method for the synthesis of guanidino-sugars. The methodology described herein is one of the few existing general methodologies for the formation of medium-sized ex...

Descripción completa

Detalles Bibliográficos
Autores: Santana, Andrés G., González Martín, Concepción C.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/221650
Acceso en línea:http://hdl.handle.net/10261/221650
Access Level:acceso abierto
Palabra clave:Photodissociation
Guanidine
Carbohydrates
Cyclization
Chemical structure
id ES_08c9356ab1bf2425e3b573e1d6bbc992
oai_identifier_str oai:digital.csic.es:10261/221650
network_acronym_str ES
network_name_str España
repository_id_str
spelling Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated HeterocyclesSantana, Andrés G.González Martín, Concepción C.PhotodissociationGuanidineCarbohydratesCyclizationChemical structureThe fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent cyclization promoted by hypervalent iodine provide an excellent method for the synthesis of guanidino-sugars. The methodology described herein is one of the few existing general methodologies for the formation of medium-sized exo- and endoguanidine-containing heterocycles presenting a high degree of oxygenation in their structure.This research study was supported by Mineco/Feder (SAF2013-48399-R). A.G.S. thanks the I3P-CSIC Program for a fellowship and MINECO for a JdC-incorporacion contract.Peer reviewedAmerican Chemical SocietyMinisterio de Asuntos Económicos y Transformación Digital (España)Consejo Superior de Investigaciones Científicas (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/221650reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#MINECO/SAF2013/48399-Rhttps://doi.org/10.1021/acs.orglett.0c03091Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2216502026-05-22T06:33:51Z
dc.title.none.fl_str_mv Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
title Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
spellingShingle Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
Santana, Andrés G.
Photodissociation
Guanidine
Carbohydrates
Cyclization
Chemical structure
title_short Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
title_full Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
title_fullStr Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
title_full_unstemmed Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
title_sort Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles
dc.creator.none.fl_str_mv Santana, Andrés G.
González Martín, Concepción C.
author Santana, Andrés G.
author_facet Santana, Andrés G.
González Martín, Concepción C.
author_role author
author2 González Martín, Concepción C.
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Asuntos Económicos y Transformación Digital (España)
Consejo Superior de Investigaciones Científicas (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Photodissociation
Guanidine
Carbohydrates
Cyclization
Chemical structure
topic Photodissociation
Guanidine
Carbohydrates
Cyclization
Chemical structure
description The fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent cyclization promoted by hypervalent iodine provide an excellent method for the synthesis of guanidino-sugars. The methodology described herein is one of the few existing general methodologies for the formation of medium-sized exo- and endoguanidine-containing heterocycles presenting a high degree of oxygenation in their structure.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/221650
url http://hdl.handle.net/10261/221650
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
MINECO/SAF2013/48399-R
https://doi.org/10.1021/acs.orglett.0c03091
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869403065778438144
score 15,811543

Similares en LA Referencia