反应详情

To a stirred suspension of sodium hydride (1.67 g, 41.6 mmol) in 100 mL of dry THF was added at 0° C. a solution of methyl 6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside (4.0 g, 9.25 mmol) in 50 mL of dry THF. After 5 minutes, the suspension was warmed to room temperature and stirred for 1 hour. Benzyl bromide (5.50 mL, 46.2 mmol) was added at room temperature followed by tetrabutylammonium iodide (341 mg, 0.93 mmol). The suspension was warmed to 50° C. and stirred for 4 days. After quenching with 40 mL of saturated aqueous ammonium chloride, the resulting mixture was diluted with ether (600 mL) and washed with H2O (2×200 mL), saturated aqueous NaCl (1×200 mL), and dried over magnesium sulfate. Concentration and flash chromatography (silica, 10% ether in petroleum ether) provided pure target compound (4.48 g, 69%) as a clear oil.

1. temperatureThe suspension was warmed to 50° C.
2. stirringstirred for 4 days
3. customAfter quenching with 40 mL of saturated aqueous ammonium chloride
4. additionthe resulting mixture was diluted with ether (600 mL)
5. washwashed with H2O (2×200 mL), saturated aqueous NaCl (1×200 mL)
6. dry with materialdried over magnesium sulfate
7. concentrationConcentration and flash chromatography (silica, 10% ether in petroleum ether)