3-O-BENZYL-1,2-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE5,6-CARBONATE

3-O-BENZYL-1,2-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE5,6-CARBONATE Chemische Eigenschaften,Einsatz,Produktion Methoden

• synthetische

  A three-necked, round-bottomed flask was charged with 3-O-benzyl-1,2-Oisopropylidene- α-d-glucofuranose 907 (35.94 g, 115.84 mmol) and dry pyridine (110 mL). The solution was cooled to an internal temperature of +5 ℃, and then triphosgene (11.50 g, 38.76 mmol) was added in portions, using an addition funnel for solids, over a period of 80 min. Stirring was continued for 1 h. The reaction mixture was then diluted with chloroform (550 mL) and washed with water (1×220 mL, 1 ×150 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by azeotropic distillation with toluene (2×60 mL) and dried in vacuo overnight. The product was purified on a flash chromatography column, eluting with EtOAc/ hexanes (25:75 → 100:0). The appropriate fractions were combined and concentrated. The product 908 was isolated in 89% yield.