Partial methylation of methyl α-D- and β-D-threofuranoside

Abstract

The methylation rate of hydroxyl groups of the title glycosides I and II has been studied in their reaction with methyl iodide and sodium hydroxide in acetonitrile. From the relative rate constants determined for the side and consecutive reactions taking place the differences in methylation rate of the individual hydroxyl groups have been deduced and are discussed from the standpoint of possible steric and polar effects.