Effect of base concentration upon the reactivities of the hydroxyl groups in methyl D-glucopyranosides.

The anomeric methyl D-glucopyranosides were treated with NJV-diethylaziridinium chloride in various molarities of aqueous sodium hydroxide at variable ionic strength and constant ionic strength. It was found that the extent of reaction of the hydroxyl groups at C-2, C-3, and C-4 decreased with increasing concentration of base. Reaction at the C-6 hydroxyl group remained essentially constant with increasing concentration of base. Neither varying the ionic strength nor the concentration of reagent affected the distribution of substituents at any given concentration of base.