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  • Title: Carbohydrate-derived spiroketals. Stereoselective synthesis of di-D-fructose dianhydrides by boron trifluoride promoted glycosylation-spiroketalization of acetal precursors.
    Author: Benito JM, Gómez-García M, Ortiz Mellet C, García Fernández JM, Defaye J.
    Journal: Org Lett; 2001 Feb 22; 3(4):549-52. PubMed ID: 11178822.
    Abstract:
    [reaction: see text] Di-D-fructose 1,2':2,1'-dianhydrides, dispiro-tricyclic disaccharides widely found in food materials, have been stereoselectively prepared in one-pot reaction from O-protected D-fructose 1,2-acetonide precursors by treatment with boron trifluoride diethyl etherate. The dimerization sequence involves (i) cleavage of the anomeric acetal linkage, (ii) autoglycosylation, and (iii) final spiroketalization, the stereochemical outcome being strongly dependent on the nature of the hydroxyl protecting groups.
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