title: A new type of rearrangement in branched-chain carbohydrates: isomerization of 3-C-branched aldoses.
abstract: A new type of rearrangement is described for 3-C-branched chain aldoses. The studied transformation is based on the Mo(VI)-catalyzed isomerization of carbohydrate carbon skeleton and allows preparation of C-3 isomers of 3-C-branched aldoses in a simple way without formation of side products. This rearrangement at C-3 carbon differs from the previously described epimerization at C-2 of aldoses catalyzed by Mo(VI) ions, known as Bílik reaction. The potential of this new transformation is illustrated on the preparation of new, 3-C-methyl-D-glucose and 3-C-vinyl-D-glucose from 3-C-methyl-d-allose and 3-C-vinyl-D-allose, respectively.
authors: Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovakia. zuzana.hricoviniova@savba.sk
authors: Zuzana
authors: Z
authors: Hricovíniová
authors: Miloš
authors: M
authors: Hricovíni
mesh_terms: D002236:Carbohydrate Conformation; D002384:Catalysis; D007536:Isomerism; D008872:Microwaves; D008958:Models, Molecular; D008982:Molybdenum / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*
chemical_list: D009005:Monosaccharides; D008982:Molybdenum