New Synthetic Methods and Reagents for Complex Carbohydrates. IX. Aryl d-Glucopyranosides and 1-Aryl-1-deoxy-d-glucopyranoses from 2,3,4,6-Tetra-O-benzyl-α-d-glucopyranosyl Dimethylphosphinothioate

The reactions of 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl dimethylphosphinothioate and phenolic compounds gave the corresponding aryl α-d-glucopyranosides predominantly in good yields, even when the trimethylsiloxy derivatives of benzene, which are known to afford 1-aryl-1-deoxy-d-glucopyranoses by the conventional methods, were used as acceptors. On the other hands, 1-ary-1-deoxy-β-d-glucopyranose was obtained in good yield when 1,3,5-trimethoxybenzene was used as an acceptor.