The separation of methyl ethers of methyl 2-acetamido-2-deoxy-D-glucopyranosides on a strongly basic ion-exchange...

The methyl ethers of methyl 2-acetamido-2-deoxy-alpha- and -beta-D-glucopyranoside can be isolated on a preparative scale by chromatography on Dowex-1(HO-) resin. This procedure greatly simplifies the purification of methyl ethers, and has been used to isolate the methyl ethers produced by partial methylation of methyl 2-acetamido-2-deoxy-beta-D-glucopyranoside. The separations are thought to depend on an ion-exchange process in which all the free hydroxyl groups are involved. It is concluded that the following acidity sequence holds: HO-4 greater than HO-3 greater than HO-6.