1: 40 percent / LDA, n-BuLi, HMPT / tetrahydrofuran; hexane / 1) -20 deg C, 10 min, 2) 20 deg C, 2+20 h 2: 40 percent / Na/Hg / methanol / 48 h / 25 °C 3: 65 percent / CsF / tetrahydrofuran / 3 h / Heating View Scheme

1: 75 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 82 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme

1: sodium azide / N,N-dimethyl-formamide / 19 h / 20 °C 2: trimethylphosphane; sodium hydroxide / water; methanol / 15 h / 40 °C 3: N-ethyl-N,N-diisopropylamine / methanol / 15 h / 0 - 20 °C 4: anhydrous potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C / |Inert atmosphere 2: anhydrous potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C / |Inert atmosphere 3: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / chloroform / 12 h / 0 - 20 °C 4: N-ethyl-N,N-diisopropylamine / chloroform / 40 h / 20 °C 5: recombinant human acid ceramidase / aq. acetate buffer / 2.5 h / 37 °C / |Enzymatic reaction View Scheme

2,2'-azo-bisisobutyronitrile; 1-((dibutylstannyl)hexyl)-3-methyl-1H-imidazol-3-ium iodide in acetonitrile T=80°C; 6 h; Inert atmosphere; chemoselective reaction;

1: 75 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 82 percent / aq. H2O2 / tetrahydrofuran / 24 h 4: aq. KOH / 0.5 h / Heating View Scheme

1: 75 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 82 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme

sodium hydrogencarbonate; sodium iodide in acetone 3 h; Heating;

T=160°C; und Verseifen des Reaktionsprodukts mit methylalkoholischer Kalilauge;

1: sodium azide / N,N-dimethyl-formamide / 19 h / 20 °C 2: trimethylphosphane; sodium hydroxide / water; methanol / 15 h / 40 °C View Scheme