tetrabutyl ammonium fluoride in tetrahydrofuran 1 h; Ambient temperature;

1: 44 percent / sodium phosphate, m-CPBA / CHCl3 / 43 h / Ambient temperature 2: 30 percent / NaBH4 / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h 3: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 4: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 79 percent / NaBH4, CeCl3*7H2O / ethanol / 1.5 h / 0 - 20 °C 2: Et3N, DMAP / CH2Cl2 / 50 h / Heating 3: sodium phosphate, tetrabutylammonium periodate / CHCl3 / 24 h 4: 44 percent / sodium phosphate, m-CPBA / CHCl3 / 43 h / Ambient temperature 5: 30 percent / NaBH4 / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h 6: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 7: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: Et3N, DMAP / CH2Cl2 / 50 h / Heating 2: sodium phosphate, tetrabutylammonium periodate / CHCl3 / 24 h 3: 44 percent / sodium phosphate, m-CPBA / CHCl3 / 43 h / Ambient temperature 4: 30 percent / NaBH4 / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h 5: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 6: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 30 percent / NaBH4 / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h 2: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 3: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: sodium phosphate, tetrabutylammonium periodate / CHCl3 / 24 h 2: 44 percent / sodium phosphate, m-CPBA / CHCl3 / 43 h / Ambient temperature 3: 30 percent / NaBH4 / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h 4: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 5: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl3 / 14 h / Ambient temperature 2: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

sodium periodate; tetrabutylammomium bromide in dichloromethane; water 0.166667 h; Ambient temperature;