Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose

C Müller, V Diehl, FW Lichtenthaler

Index: Mueller, Christoph; Diehl, Volker; Lichtenthaler, Frieder W. Tetrahedron, 1998 , vol. 54, # 36 p. 10703 - 10712

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Citation Number: 46

Abstract

Brief exposure to bromine in water-methanol at 0° C smoothly and effectively converts furfurylamines with hydroxymethy (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3-pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one- pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D- ...