Collect. Czech. Chem. Commun. 1980, 45, 1959-1963

Benzyl ethers of methyl α-D-glucopyranoside

Dušan Joniak, Božena Košíková and Ludmila Kosáková

Chemical Institute, Slovak Academy of Sciences, 809 33 Bratislava


Methyl 4-O-(3-methoxy-4-hydroxybenzyl) and methyl 4-O-(3,5-dimethoxy-4-hydroxybenzyl)-α-D-glucopyranoside and their 6-O-isomers were prepared as model substances for the ether lignin-saccharide bond by reductive cleavage of corresponding 4,6-O-benzylidene derivatives. Kinetic study of acid-catalyzed hydrolysis of the compounds prepared was carried out by spectrophotometric determination of the benzyl alcoholic groups set free, after their reaction with quinonemonochloroimide, and it showed the low stability of the p-hydroxybenzyl ether bond.