English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37869
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:

Stereoselective synthesis of nonsymmetrical difructose dianhydrides from xylylene-tethered d-fructose precursors

AuthorsLouis, Farida; García Moreno, María Isabel; Balbuena Olivia, Patricia ; Ortiz-Mellet, Carmen; García-Fernández, José Manuel
Issue Date16-Jan-2008
CitationTetrahedron 64(12): 2792-2800 (2008)
AbstractNonsymmetrical furanose–pyranose difructose dianhydrides (DFAs), a class of cyclic disaccharides present in foodstuffs, have been prepared in high yield by connecting the reacting monosaccharide moieties through a xylylene bridge prior to triflic acid-promoted bis-spiroketalization. The reaction can then proceed either intra- or intermolecularly, both the regio- and the stereoselectivity being strongly dependent on the spacer length. Noteworthy, the longer m- and p-xylylene positional isomers led to the thermodynamic α-d-fructofuranose β-d-fructopyranose 1,2′:2,1′-dyanhydride 1, the major DFA in commercial caramel, in a stereoselective manner. The shorter o-xylylene tether afforded preferentially the elusive contra-thermodynamic β-d-fructofuranose α-d-fructopyranose diastereomer 2, a trace constituent of caramel. The results have been rationalized in terms of stereoelectronic and conformational properties and offer new perspectives for the preparation of pure DFA standards for analytical and nutritional studies.
Description9 páginas, 3 figuras, 2 esquemas.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2008.01.054
Appears in Collections:(IIQ) Artículos
Files in This Item:
There are no files associated with this item.
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.