1.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium chloride; sodium hypochlorite / water; acetonitrile; aq. phosphate buffer / 35 °C / pH 6 - 7 2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 24 h / 20 °C View Scheme

sodium chlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene in acetonitrile T=0 - 20°C; pH=6.4; aq. phosphate buffer;

1.1: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.75 h 2.1: methanol; water / 2 h 3.1: manganese(IV) oxide / acetonitrile / 24 h / 60 °C 4.1: dichloromethane / 1 h / Inert atmosphere 5.1: benzotriazol-1-ol; triethylamine / dichloromethane / 0.03 h 6.1: dichloromethane / 1 h 7.1: benzotriazol-1-ol; triethylamine / dichloromethane / 0.03 h 8.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 20 °C / Inert atmosphere 10.1: methanol / 3 h 11.1: BOP-Cl; triethylamine / acetonitrile / Inert atmosphere 12.1: lithium hydroxide hydrate / tetrahydrofuran; water / 2 h / 20 °C 12.2: pH 3 13.1: dichloromethane / 2 h / 20 °C 14.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.5 h / 0 °C1.2: KO-t-Bu / tetrahydrofuran / 1 h / 20 °C2.1: aq. KOH / 3 h / 80 °C2.2: tetrahydrofuran / 6 h / 20 °C  

Multi-step reaction with 7 steps 1.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium chloride; sodium hypochlorite / water; acetonitrile; aq. phosphate buffer / 35 °C / pH 6 - 72.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C2.2: 24 h / 20 °C3.1: sulfur trioxide pyridine complex / pyridine / 2 h / 0 °C3.2: 2 h / |Reflux4.1: hydrogen; 5 palladium on charcoal / water; methanol / 1 h / 2585.81 Torr5.1: pyridine / 1.5 h / 0 - 20 °C6.1: potassium dihydrogenphosphate / water; dichloromethane / 1 h / 0 - 5 °C7.1: formic acid / dichloromethane / 0 - 20 °C