A Convenient Synthesis of 2-Deoxy-β-D-glucopyranosides

The O-(2-deoxy-2-phenylthio-α-D-glucopyranosyl) trichloroacetimidate α-3 was obtained from 3,4,6-tri-O-benzyl-D-glucal (1) in a two-step procedure. This compound is a powerful glucopyranosyl donor, which with typical alcohol acceptors provided mainly the corresponding 2-phenylthio-substituted 2-deoxy-β-D-glucopyranosides β-5a to β-5d. These were converted by Raney nickel treatment to the desired 2-deoxy-β-D-glucopyranosides 6 in high yields.