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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37655
Title: 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
Molecular structure
Spiro compounds
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
URI: http://hdl.handle.net/10261/37655
DOI: 10.1021/ol0474094
ISSN: 1523-7060
References: 15704936
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