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Closed Access item Spacer-Mediated Synthesis of Bis-spiroketal Disaccharides: Nonsymmetrical Furanose-Pyranose Difructose Dianhydrides

Authors:Louis, Farida
García Moreno, María Isabel
Balbuena Olivia, Patricia
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
Keywords:Acetals, Difructose dianhydrides, Spiroacetals, Oligosaccharides, Spiro compounds
Issue Date:25-Sep-2007
Publisher:Georg Thieme Verlag
Citation:Synlett (17): 2738-2742 (2007)
Abstract:The stereochemical outcome of the dimerization reaction of D-fructose, leading to tricyclic bis-spiroketal systems, can be tuned by inserting a xylylene template between the reacting ­moieties. Spirocyclization becomes then an intramolecular process, the available conformational space depending on the nature of the tether. The methodology is here illustrated by the stereoselective synthesis of two nonsymmetrical di-D-fructose dianhydrides present in commercial caramel.
Description:5 páginas, 2 figuras, 2 esquemas.
Publisher version (URL):http://dx.doi.org/10.1055/s-2007-991055
Appears in Collections:(IIQ) Artículos

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