title: Rearrangement of unsaturated 2,4-O-benzylidenehexitol derivatives into C-glycosylbenzene derivatives.
abstract: Acetolysis of (Z)-1,3-di-O-acetyl-2,4-O-benzylidene-6-C-(2,4-dichlorophenyl)-D-xylo-he x- 5-enitol (3) afforded (E)-1,2,3,4-tetra-O-acetyl-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enit ol and 2-C-[(R)-acetoxy(2,4-dichlorophenyl)methyl]-3,4,6-tri-O-acetyl-2-deoxy- beta-L-galacto- and -beta-L-gulo-hexopyranosylbenzene. The mechanism of this new rearrangement was studied by exchanging the substituents at C-1 and C-3 in 3 and those of the aromatic ring attached to C-6.
authors.affiliation: Institute for Drug Research, Budapest, Hungary.
authors.forename: J
authors.initials: J
authors.lastname: Kuszmann
authors.forename: B
authors.initials: B
authors.lastname: Podányi
authors.forename: G
authors.initials: G
authors.lastname: Jerkovich
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors
chemical_list: D001555:Benzene Derivatives; D001597:Benzylidene Compounds; D006601:Hexoses; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors