Rearrangement of unsaturated 2,4-O-benzylidenehexitol derivatives into C-glycosylbenzene derivatives.
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.
Kuszmann
J
J
Institute for Drug Research, Budapest, Hungary.
Podányi
B
B
Jerkovich
G
G
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
D001555:Benzene Derivatives; D001597:Benzylidene Compounds; D006601:Hexoses; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors