1: 90 percent / NaHCO3; NaOAc*3H2O; NBS / tetrahydrofuran; H2O / 1 h / 0 °C 2: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C 3: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 4: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 5: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 6: 80 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C View Scheme

1.1: 76 percent / I2 / dimethylsulfoxide / 24 h / 110 °C 2.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C 2.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C 3.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 4.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 5.1: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 6.1: 80 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C View Scheme

hesperidinase; HOAc-NaOAc buffer in water T=40°C; 0.05 h;

sodium hydroxide in methanol T=23°C; 0.333333 h;

sodium hydroxide in methanol T=23°C; 0.333333 h;

T=60°C; 1 h; Irradiation;

water base;

hydrogenchloride; ethanol 1 h; Heating;

sulfuric acid in ethanol 2 h; Heating;