1,3,4,6-Tetra-O-acetyl-2-deoxy-α-D-glucopyranose could be produced through the following synthetic routes.

A 1-L, round-bottomed flask equipped with a magnetic stirring bar and a reflux condenser with a Claisen head on top fitted with a septum and a dry nitrogen inlet is charged with 20.6 g (50 mmol) of 2,3,4,6,-tetra-O-acetyl-α-D-glucopyranosyl bromide and 400 mL of anhydrous toluene. The mixture is flushed with nitrogen and brought to reflux with a hot oil bath. A nitrogen atmosphere is maintained over the well-stirred reaction mixture during this and the ensuing steps. Meanwhile, a solution of 1.64 g (10 mmol) of azobisisobutyronitrile (AIBN) and 16.0 g (55 mmol) of tributylstannane in 90 mL of anhydrous toluene is prepared and filtered if necessary. This solution is added to the refluxing, well-stirred reaction mixture during 6 hr by a syringe pump through a long needle that pierces the septum and ends at least 3 cm above the lower end of the cooling zone of the reflux condenser. Ten minutes after all of the solution is added, the reaction mixture is cooled and the solvent is removed with a rotary evaporator (bath 40°C); 100 mL of hexane and 100 mL of acetonitrile are added, and the resulting two-phase solution is stirred vigorously for 5 min and then transferred to a separatory funnel. The lower, acetonitrile layer is separated and the hexane phase washed with 10 mL of acetonitrile. This extraction of the combined acetonitrile solutions is repeated twice using 100 mL of hexane each time. The combined acetonitrile phases are then filtered and distilled (rotary evaporator, bath temp. 40°C). Coevaporation with 40 mL of hexane yields crude solid material that is dissolved in 120 mL of boiling tert-butyl methyl ether. Then 30 mL of hexane is added and the mixture is left for 4 hr at room temperature. To complete crystallization of the product, another 20 mL of hexane is added and the mixture is kept for 12 hr at 5°C. The long, colorless needles are filtered and washed once with 30 mL of hexane/tert-butyl methyl ether (2:1) and two times with 30 mL of pentane to yield 13.2–13.4 g (79–81%) of 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranose, mp 109–110°C; [α]_D20 + 113°C (C₂H₅OH, c 1.2).