sodium hypochlorite; sodium chlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical in phosphate buffer; acetonitrile T=45°C; pH=6.7; 24 h;

hydrogen; 10percent Pd/C in ethanol T=20°C;

1: aqueous NaOH / tetrahydrofuran; H2O / 20 °C 2: 6.17 g / Et3N / tetrahydrofuran / 0 - 20 °C 3: 84 percent / chromium trioxide; pyridine / CH2Cl2 / 4 h / 20 °C 4: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 5: 2.97 g / aqueous NH4Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6: 78 percent / thionyl chloride; pyridine / 0.33 h / Heating 7: 90 percent / hydrogen / 10percent Pd/C / ethanol / 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: 94 percent / trichloroisocyanuric acid; 2,2,6,6-tetramethyl-1-piperidinoxyl / CH2Cl2 / 0.33 h / 0 °C 2: 56 percent / tetrabutylammonium fluoride / 24 h / 0 - 20 °C 3: 94 percent / NaBH4; LiCl / ethanol; tetrahydrofuran / 18 h / 20 °C 4: 89 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 18 h / 20 °C 5: NaH / tetrahydrofuran / 2 h / 0 - 20 °C 6: potassium tert-butoxide / tetrahydrofuran / 2 h / -40 °C 7: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 8: H2 / Raney-Ni / methanol 9: 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: 56 percent / tetrabutylammonium fluoride / 24 h / 0 - 20 °C 2: 94 percent / NaBH4; LiCl / ethanol; tetrahydrofuran / 18 h / 20 °C 3: 89 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 18 h / 20 °C 4: NaH / tetrahydrofuran / 2 h / 0 - 20 °C 5: potassium tert-butoxide / tetrahydrofuran / 2 h / -40 °C 6: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 7: H2 / Raney-Ni / methanol 8: 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: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 2: H2 / Raney-Ni / methanol 3: 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: H2 / Raney-Ni / methanol 2: 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: 6.17 g / Et3N / tetrahydrofuran / 0 - 20 °C 2: 84 percent / chromium trioxide; pyridine / CH2Cl2 / 4 h / 20 °C 3: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 4: 2.97 g / aqueous NH4Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5: 78 percent / thionyl chloride; pyridine / 0.33 h / Heating 6: 90 percent / hydrogen / 10percent Pd/C / ethanol / 20 °C View Scheme

1: 84 percent / chromium trioxide; pyridine / CH2Cl2 / 4 h / 20 °C 2: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 3: 2.97 g / aqueous NH4Cl; tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4: 78 percent / thionyl chloride; pyridine / 0.33 h / Heating 5: 90 percent / hydrogen / 10percent Pd/C / ethanol / 20 °C View Scheme