2,4-Bis(benzyloxy)-6-chloro-1,3,5-triazine

Experimental procedure¹⁾: 2,4-bis(benzyloxy)-6-chloro-1,3,5-triazine (1, 12.3 g, 37.5 mmol) is added to a solution of D-glucose (4.5 g, 25 mmol), N-methylmorpholine (4.1 mL, 38 mmol) and ammonia (3.3 mL, 50 mmol, 29% aqueous solution) in the mixture of acetonitrile and water (125 mL, CH₃CN:H₂O = 1:1) and the resulting mixture is stirred for 3 h at 0 °C. After concentration in vacuo, the residue is washed with water and chloroform. The filtrate is concentrated in vacuo to give β-glucoside (9.42 g, 20.0 mmol, 80 % yield).
  Excess amount of alcohol is added to the mixture of β-glucoside (0.2 mmol) and Pd/C (5 mg). Under hydrogen atmosphere, the resulting mixture is stirred at room temperature. The reaction mixture is filtered, and the filtrate is concentrated in vacuo to afford the alkoxy group substituted glucosides.