1: NaBH4 / Heating 2: NaIO4 / ethanol 3: pyridine 4: MCPBA / CHCl3 5: (i) (PhSe)2, NaBH4, (ii) NaIO4 7: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: MCPBA / CHCl3 2: (i) (PhSe)2, NaBH4, (ii) NaIO4 4: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: (i) (PhSe)2, NaBH4, (ii) NaIO4 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: NaIO4 / ethanol 2: pyridine 3: MCPBA / CHCl3 4: (i) (PhSe)2, NaBH4, (ii) NaIO4 6: LiAlH4 / tetrahydrofuran / Heating View Scheme

anschliessend Behandeln mit NaCl und wss. HCl;

hydrogen; platinum on activated charcoal in acetic acid P=1471.02 Torr; Ambient temperature;

1.1: pyridine / Inert atmosphere 2.1: [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide / acetonitrile / Inert atmosphere 3.1: water; lithium hydroxide hydrate / tetrahydrofuran / 18 °C / Inert atmosphere 3.2: Amberlyst 15 ion exchange resin / 1 h / Inert atmosphere 4.1: pyridine; thionyl chloride / 4 h / 20 °C / Inert atmosphere View Scheme

trichlorophosphate Yield given. Yields of byproduct given;

1: (i) MeOH, (ii) Ag2O, H2O 2: OsO4 / pyridine; diethyl ether 3: (i) NaIO4, AcOH, NaOAc, (ii) As2O3, H2O, (iii) KMnO4, dioxan 4: Cu2Cr2O3 / quinoline View Scheme