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Closed Access item Rigid Spacer-Mediated Synthesis of Bis-Spiroketal Ring Systems: Stereoselective Synthesis of Nonsymmetrical Spiro Disaccharides

Authors:Rubio Castillo, Enrique Miguel
García Moreno, María Isabel
Balbuena Olivia, Patricia
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
Keywords:Carbohydrates, Disaccharides, Molecular structure, Spiro compounds, Caramels, Xylylene
Issue Date:25-Jan-2005
Publisher:American Chemical Society
Citation:Organic Letters 7(4): 729-731 (2005)
Abstract:The application of the "rigid spacer-mediated linkage between nonreacting centers" concept to the preparation of nonsymmetrical bis-spiroketal structures is demonstrated by the stereoselective synthesis of the bis-spiro fructodisaccharide 1, a minor component of industrial caramels. An o-xylylene bridge has been used to limit the conformational space during the intramolecular glycosylation-spirocyclization reaction of a difructopyranose precursor, thus controlling both the ring size and the stereochemistry at the spiro centers.
Description:3 páginas, 1 figura, 2 esquemas.
Publisher version (URL):http://dx.doi.org/10.1021/ol0474094
Appears in Collections:(IIQ) Artículos

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