Stereospecific Synthesis of Aryl β-D-N-Acetylglucopyranosides by Phase Transfer Catalysis

Abstract

Under phase transfer catalyzed conditions, 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (1) reacts with a series of phenoxides to afford high yields of acetylated aryl β-D-N-acetylgluco-pyranosides (3–8). Deprotection of the hydroxyl groups under Zemplén condition gave quantitative yields of the free glycosides 3a-8a.