1: 99 percent / Et3N / tetrahydrofuran; H2O / 12 h / Ambient temperature 2: 99 percent / Et3N, DMAP / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) r.t., 2 h View Scheme

1: 99 percent / Et3N / CH2Cl2 / 4 h / 0 °C 2: 91 percent / (COCl)2; Et3N; DMSO / CH2Cl2 / -40 - 20 °C 3: 89 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C View Scheme

1: 94 percent / triethylamine / CH2Cl2 / 18 h 2: 94 percent / trichloroisocyanuric acid; 2,2,6,6-tetramethyl-1-piperidinoxyl / CH2Cl2 / 0.33 h / 0 °C 3: 56 percent / tetrabutylammonium fluoride / 24 h / 0 - 20 °C 4: 94 percent / NaBH4; LiCl / ethanol; tetrahydrofuran / 18 h / 20 °C 5: 89 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 18 h / 20 °C 6: NaH / tetrahydrofuran / 2 h / 0 - 20 °C 7: potassium tert-butoxide / tetrahydrofuran / 2 h / -40 °C 8: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 9: H2 / Raney-Ni / methanol 10: 94 percent / NaOCl; NaClO2; 2,2,6,6-tetramethyl-1-piperidinoxyl / acetonitrile; aq. phosphate buffer / 24 h / 45 °C / pH 6.7 View Scheme

1: 47.0 g / aq. NaHCO3 / dioxane / 4 h / 20 °C 2: 91 percent / pyridine; 4-dimethylaminopyridine / 144 h / 20 °C 3: 97 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / Heating 4: 70 percent / aq. H2O2; pyridine / CH2Cl2 / 2 h / 20 °C 5: H2 / PtO2 / methanol / 12 h / 1520 Torr View Scheme