Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/155721
COMPARTIR / EXPORTAR:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE

Invitar a revisión por pares abierta
Título

Stereoselective ethynylation and propargylation of chiral cyclic nitrones: application to the synthesis of glycomimetics

AutorGarcía-Viñuales, Sara CSIC; Delso, J. Ignacio CSIC ORCID; Merino, Pedro CSIC ORCID ; Tejero, Tomás CSIC ORCID
Palabras claveNitrones
Glycomimetics
Alkynes
Ethynylation
Propargylation
Fecha de publicación2016
EditorThieme
CitaciónSynthesis 48(19): 3339-3351 (2016)
ResumenEthynylation and propargylation of chiral nonracemic polyhydroxylated cyclic nitrones with Grignard reagents are efficient methods for preparing building blocks containing an alkyne moiety to be used in copper-catalyzed azide alkyne cycloaddition click chemistry. Whereas ethynylation takes place with excellent diastereoselectivity, propargylation afforded mixtures of diastereomers in some cases. The use of (trimethylsilyl)propargyl bromide as precursor of the Grignard reagent is necessary to avoid the formation of undesired allene derivatives. DFT calculations explain, within the experimental error, the observed behavior. Cycloaddition of the obtained pyrrolidinyl alkynes with sugar azides derived from β-(1,3)-glucans provides glycomimetics suitable to be used against fungal transglycosylases.
Versión del editorhttps://doi.org/10.1055/s-0035-1562500
URIhttp://hdl.handle.net/10261/155721
DOI10.1055/s-0035-1562500
Identificadoresdoi: 10.1055/s-0035-1562500
e-issn: 1437-210X
issn: 0039-7881
Aparece en las colecciones: (ISQCH) Artículos




Ficheros en este ítem:
Fichero Descripción Tamaño Formato
Synthesis Glycomimetics.pdf367,76 kBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo

CORE Recommender

SCOPUSTM   
Citations

10
checked on 19-mar-2024

WEB OF SCIENCETM
Citations

6
checked on 24-feb-2024

Page view(s)

284
checked on 28-mar-2024

Download(s)

430
checked on 28-mar-2024

Google ScholarTM

Check

Altmetric

Altmetric


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.