potassium carbonate in methanol 0.5 h; Ambient temperature;

1: 1.) NaH / 1.) n-hexane, THF, 0 deg C, 15 min, 2.) n-hexane, THF, 0 deg C, 30 min 2: 77 percent / K2CO3 / methanol / 0.5 h / Ambient temperature View Scheme

1: 98 percent / pyridine, 4-dimethylaminopyridine / 0.25 h / Ambient temperature 2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, RT, 30 min 3: 1.) NaH / 1.) n-hexane, THF, 0 deg C, 15 min, 2.) n-hexane, THF, 0 deg C, 30 min 4: 77 percent / K2CO3 / methanol / 0.5 h / Ambient temperature View Scheme

1: 25 percent / β-glucosidase, phosphate buffer, pH 5 / 24 h / 30 °C 2: 98 percent / pyridine, 4-dimethylaminopyridine / 0.25 h / Ambient temperature 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, RT, 30 min 4: 1.) NaH / 1.) n-hexane, THF, 0 deg C, 15 min, 2.) n-hexane, THF, 0 deg C, 30 min 5: 77 percent / K2CO3 / methanol / 0.5 h / Ambient temperature View Scheme