hydrogenchloride in ethylene glycol T=110°C; 2 h;

intestinal gut bacteria in a human fecal suspension T=37°C; 5 h; Enzymatic reaction;

1: Et3N / CH2Cl2 2: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 3: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

1: 96 percent / 5percent aqueous HF / tetrahydrofuran 2: Et3N / CH2Cl2 3: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 4: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

1: tetrahydrofuran / Ambient temperature 2: 96 percent / 5percent aqueous HF / tetrahydrofuran 3: Et3N / CH2Cl2 4: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 5: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

1: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 2: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 3: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: Ac2O / CH2Cl2 / 3.5 h / Heating 2: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 3: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 4: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 4: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 5: Ac2O / CH2Cl2 / 3.5 h / Heating 6: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 7: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 8: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 2: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 3: Ac2O / CH2Cl2 / 3.5 h / Heating 4: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 5: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 6: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 2: Ac2O / CH2Cl2 / 3.5 h / Heating 3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 4: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme