pyridine; β-glucosidase Multistep reaction;

sodium methylate in methanol T=0°C; 0.0833333 h;

1.1: 62 percent / AgOTf3; 4 Angstroem molecular sieves; 2,6-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C 2.1: 82 percent / CF3COOH / 1,2-dichloro-ethane / 12 h / 20 °C 3.1: MeONa / methanol / 1 h / 20 °C 3.2: 96 percent / 4-(dimethylamino)pyridine / 3 h / 20 °C 4.1: 61 percent / acetonitrile / 0.22 h / Irradiation 5.1: 92 percent / MeONa / methanol / 0.08 h / 0 °C View Scheme

1: 61 percent / acetonitrile / 0.22 h / Irradiation 2: 92 percent / MeONa / methanol / 0.08 h / 0 °C View Scheme

1.1: MeONa / methanol / 1 h / 20 °C 1.2: 96 percent / 4-(dimethylamino)pyridine / 3 h / 20 °C 2.1: 61 percent / acetonitrile / 0.22 h / Irradiation 3.1: 92 percent / MeONa / methanol / 0.08 h / 0 °C View Scheme

1.1: 82 percent / CF3COOH / 1,2-dichloro-ethane / 12 h / 20 °C 2.1: MeONa / methanol / 1 h / 20 °C 2.2: 96 percent / 4-(dimethylamino)pyridine / 3 h / 20 °C 3.1: 61 percent / acetonitrile / 0.22 h / Irradiation 4.1: 92 percent / MeONa / methanol / 0.08 h / 0 °C View Scheme