tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; desilylation; 0.5 h;

1.1: CF3COOH / H2O / 0.5 h / 0 °C 2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C 2.2: CeCl3 / tetrahydrofuran; hexane / 1 h / -78 °C 2.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C 3.1: 82 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C 1.2: CeCl3 / tetrahydrofuran; hexane / 1 h / -78 °C 1.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: 82 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C View Scheme

1: trifluoroacetic acid / H2O / 6 h / 20 °C 2: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C 3: 90 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 21 h / 60 °C 4: 77 percent / NH3 / methanol / 46 h / 20 °C View Scheme

1: 7.17 g / sodium borohydride / methanol / 6.5 h / 20 °C 2: pyridine; 4-(dimethylamino)pyridine / 5 h / 20 °C 3: trifluoroacetic acid / H2O / 6 h / 20 °C 4: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C 5: 90 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 21 h / 60 °C 6: 77 percent / NH3 / methanol / 46 h / 20 °C View Scheme

1: sodium periodate / methanol; H2O / 15 h / 20 °C 2: 7.17 g / sodium borohydride / methanol / 6.5 h / 20 °C 3: pyridine; 4-(dimethylamino)pyridine / 5 h / 20 °C 4: trifluoroacetic acid / H2O / 6 h / 20 °C 5: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C 6: 90 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 21 h / 60 °C 7: 77 percent / NH3 / methanol / 46 h / 20 °C View Scheme

1: acetic acid / H2O / 24 h / 20 °C 2: sodium periodate / methanol; H2O / 15 h / 20 °C 3: 7.17 g / sodium borohydride / methanol / 6.5 h / 20 °C 4: pyridine; 4-(dimethylamino)pyridine / 5 h / 20 °C 5: trifluoroacetic acid / H2O / 6 h / 20 °C 6: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C 7: 90 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 21 h / 60 °C 8: 77 percent / NH3 / methanol / 46 h / 20 °C View Scheme

1: 1) BuLi / THF, -78 deg C 2: Bu4NF / tetrahydrofuran / Ambient temperature 3: pyridine / Ambient temperature 4: aq. HCl / Ambient temperature 5: DMAP, pyridine / 100 °C 6: 93 percent / H2SO4 / acetic acid / Ambient temperature 7: 95 percent / trimethylsilyl triflate / acetonitrile / 0 - 20 °C 8: 85 percent / NH3 / methanol / Ambient temperature View Scheme

1: DMAP, pyridine / 100 °C 2: 93 percent / H2SO4 / acetic acid / Ambient temperature 3: 95 percent / trimethylsilyl triflate / acetonitrile / 0 - 20 °C 4: 85 percent / NH3 / methanol / Ambient temperature View Scheme

1: aq. HCl / Ambient temperature 2: DMAP, pyridine / 100 °C 3: 93 percent / H2SO4 / acetic acid / Ambient temperature 4: 95 percent / trimethylsilyl triflate / acetonitrile / 0 - 20 °C 5: 85 percent / NH3 / methanol / Ambient temperature View Scheme