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  • Title: Rigid spacer-mediated synthesis of bis-spiroketal ring systems: stereoselective synthesis of nonsymmetrical spiro disaccharides.
    Author: Rubio EM, García-Moreno MI, Balbuena P, Mellet CO, García Fernández JM.
    Journal: Org Lett; 2005 Feb 17; 7(4):729-31. PubMed ID: 15704936.
    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. [Structure: see text]
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