English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/113922
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Title

Ferrier-Nicholas pyranosidic cations: application to diversity-oriented synthesis

AuthorsLópez, J. Cristobal; Lobo, Fernando ; Miranda, Silvia; Uriel, Clara ; Gómez, Ana M.
KeywordsDiversity-oriented synthesis
Stereocontrolled synthesis
Pyranosidic cations
Nicholas reaction
ICS-27
Carbohydrates
Tandem reactions
Ferrrier reaction
Glycosylation
Issue Date2014
PublisherMarcel Dekker
CitationJournal of Macromolecular Science - Pure and Applied Chemistry 86: 1357-1364 (2014)
AbstractPyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF3,OEt2, and display a remarkable reactivity leading to a variety of products. The substituent at O-6 in these glycals plays a pivotal role in directing the outcome of the transformations. Accordingly, 6-O-benzyl or 6-O-allyl groups cause a series of transformations resulting in the stereoselective formation of oxepanes through a process that involves an initial hydride transfer step from the allyl or benzyl substituent to the Ferrier-Nicholas cation. On the contrary, 6-OH derivatives undergo an overall ring contraction to branched tetrahydrofuran derivatives. 6-O-Silyl derivatives, in the presence of heteroaryl nucleophiles, were transformed into C-3 branched bis-C-C-glycosides, containing two of such molecules.
URIhttp://hdl.handle.net/10261/113922
DOI10.1515/pac-2014-0402
Identifiersdoi: 10.1515/pac-2014-0402
issn: 1060-1325
e-issn: 1520-5738
Appears in Collections:(IQOG) Artículos
Files in This Item:
File Description SizeFormat 
accesoRestringido.pdf15,38 kBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.