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DOI: 10.1039/A801955J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1751-1752

Synthesis of symmetric difucopyranose dianhydrides

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Michael Ludewig, Daniel Lazarević, Jürgen Kopf and Joachim Thiem

Abstract

By activation of methyl 3,4-O-isopropylidene-1-methyl thio-β-L-fucopyranoside (1) with copper bromide–tetrabutylammonium bromide, bis(3,4-O-isopropylidene-α-L->fucopyranose)-1,2′∶1′,2->dianhydride (2) with almost> C2-symmetry was obtained. Starting with the monosaccharide precursors 3 and 4 a corresponding activation led to the disaccharide derivative 5 which in turn was converted into the mixed D,L-dianhydride 7 employing an intramolecular imidate glycosylation.

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