1: 53 percent / oxygen, thiourea, rose bengal / methanol / Irradiation; 1.) 3 h; 2.) in the dark without oxygen, 16 h 2: 96.4 percent / 4-(dimethylamino)pyridine / CH2Cl2; pyridine / 1.) 0 deg C,; 2.) room temperature 13 h 3: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 4: 99 percent / p-toluenesulfonic acid hydrate / 60 h 5: 99 percent / KOH / methanol / 0.5 h 6: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 7: 1.) n-BuLi, triphenylmethane / 1.) hexane-THF, 0 deg C, 15 min; 2.) hexane-THF, -78 deg C,15 min 8: 98 percent / silica gel / toluene / 9 h / Heating View Scheme

1: 99 percent / KOH / methanol / 0.5 h 2: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 3: 1.) n-BuLi, triphenylmethane / 1.) hexane-THF, 0 deg C, 15 min; 2.) hexane-THF, -78 deg C,15 min 4: 98 percent / silica gel / toluene / 9 h / Heating View Scheme

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-65°C; Swern oxidation;

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-65°C; Swern oxidation;

2: porcine pancreatic lipase 3: OsO4, N-methylmorpholine N-oxide 4: TsOH 5: H2 / Pd/C 6: 88 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH2Cl2 View Scheme

1.1: CH3PPh3Br; t-BuOK / tetrahydrofuran 1.2: 65 percent / NaIO4 / CH2Cl2; H2O 2.1: 84 percent / tetrahydrofuran / -78 °C 3.1: Grubbs first generation catalyst / CH2Cl2 / 4 h / 20 °C 3.2: 87 percent / PCC / CH2Cl2 / 12 h View Scheme

暂无反应条件数据

sodium periodate T=20°C; 0.5 h;

sodium periodate T=20°C; 0.5 h;

1: 91 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 3 h / Heating 2: 75 percent / dicyclohexylcarbodiimide; CF3CO2H; pyridine / DMSO / toluene / 10 h / 20 °C 3: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C 4: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 5: aq. NaIO4 / 0.58 h / 0 - 20 °C 6: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C 8: 8.3 g / 4 Angstroem molecular sieves; pyridinium dichromate; AcOH / CH2Cl2 / 12 h / 24 °C View Scheme