NEW SYNTHESES OF PLANT ARYL GLYCOSIDES AS POTENTIAL GENE INDUCERS

Aryl β-d-glycopyranosides have been synthesized by coupling acetovanillone (4-hydroxy-3-methoxyacetophenone) with d-glucose, d-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with d-glucose and d-galactose; syringaldehyde (3-methoxyvanillin) with d-glucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with d-glucose. The Mauthner's procedure using peracetylated glycosyl bromides and phenolates in aqueous acetone afforded the acetylated β-d-glycosides, which were deacetylated. © 1990.