1: H2 / 5percent Pd-C / ethanol 2: 98 percent / pyridine, DMAP 3: 90 percent / acetonitrile 4: LiAlH4 / tetrahydrofuran 5: diethyl phosphorocyanidate, Et3N / dimethylformamide 6: PPTS / ethanol / 55 °C 7: Et3N / CH2Cl2 8: 1.) H2O / 2.) 65 deg C View Scheme

1: 97 percent / NaH / dimethylformamide / 17 h / Ambient temperature 2: 97 percent / aq.HCl / 1,2-dimethoxy-ethane / 1.5 h / Heating 3: 85.36 g / Et3N / tetrahydrofuran; acetonitrile / 15 h / Heating 4: 94.07 g / Et3N / CH2Cl2 / 1.5 h / -5 °C 5: dimethylformamide / 20 h / 90 °C 6: 95 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C 7: 85 percent / BF3*Et2O / CH2Cl2 / 0.75 h / -10 °C 8: Et3N / benzene / 3.5 h / Ambient temperature 9: acetonitrile / 16 h / 50 °C 10: 1.) AgNO3, pyridine, 2.) pyridine, H2S / 1.) MeOH, CH3CN, 0 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 30 min; room temperature, 1 h 11: 15.8 g / DMAP, DCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 94.07 g / Et3N / CH2Cl2 / 1.5 h / -5 °C 2: dimethylformamide / 20 h / 90 °C 3: 95 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C 4: 85 percent / BF3*Et2O / CH2Cl2 / 0.75 h / -10 °C 5: Et3N / benzene / 3.5 h / Ambient temperature 6: acetonitrile / 16 h / 50 °C 7: 1.) AgNO3, pyridine, 2.) pyridine, H2S / 1.) MeOH, CH3CN, 0 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 30 min; room temperature, 1 h 8: 15.8 g / DMAP, DCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 1.) AgNO3, pyridine, 2.) pyridine, H2S / 1.) MeOH, CH3CN, 0 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 30 min; room temperature, 1 h 2: 15.8 g / DMAP, DCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 97 percent / aq.HCl / 1,2-dimethoxy-ethane / 1.5 h / Heating 2: 85.36 g / Et3N / tetrahydrofuran; acetonitrile / 15 h / Heating 3: 94.07 g / Et3N / CH2Cl2 / 1.5 h / -5 °C 4: dimethylformamide / 20 h / 90 °C 5: 95 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C 6: 85 percent / BF3*Et2O / CH2Cl2 / 0.75 h / -10 °C 7: Et3N / benzene / 3.5 h / Ambient temperature 8: acetonitrile / 16 h / 50 °C 9: 1.) AgNO3, pyridine, 2.) pyridine, H2S / 1.) MeOH, CH3CN, 0 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 30 min; room temperature, 1 h 10: 15.8 g / DMAP, DCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane 3 h; Ambient temperature;

water 2.) 65 deg C; Yield given. Multistep reaction;