1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 5.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 5.2: 16 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 8.1: water; acetic acid / 1.5 h / Heating 9.1: pyridine / dichloromethane / 16 h / 20 °C 10.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere View Scheme

1.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 2.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 4.2: 16 h / 20 °C 5.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 6.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 7.1: water; acetic acid / 1.5 h / Heating 8.1: pyridine / dichloromethane / 16 h / 20 °C 9.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 12 h / -78 - 0 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 3.1: triethylamine / dichloromethane / 0.08 h / 20 °C 4.1: triethylamine / dichloromethane 5.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate With lithium hexamethyldisilazane in tetrahydrofuran T=-78°C; 0.5 h; 2: methyl iodide in tetrahydrofuran T=-78 - 0°C; 12 h;

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 12 h / -78 - 0 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr View Scheme