sodium periodate in tetrahydrofuran 24 h; Ambient temperature;

Multi-step reaction with 7 steps 1: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C4: concd. NH4OH / acetone / 1.5 h5: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature6: NH3, HCl / methanol / 0.08 h / Heating7: NaBH4 / methanol; tetrahydrofuran / 0.5 h  

Multi-step reaction with 5 steps 2: concd. NH4OH / acetone / 1.5 h3: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature4: NH3, HCl / methanol / 0.08 h / Heating5: NaBH4 / methanol; tetrahydrofuran / 0.5 h  

Multi-step reaction with 2 steps 1: NH3, HCl / methanol / 0.08 h / Heating2: NaBH4 / methanol; tetrahydrofuran / 0.5 h  

Multi-step reaction with 10 steps 1: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature2: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h3: LiAlH4 / diethyl ether / 3 h / Ambient temperature4: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature5: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C7: concd. NH4OH / acetone / 1.5 h8: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature9: NH3, HCl / methanol / 0.08 h / Heating10: NaBH4 / methanol; tetrahydrofuran / 0.5 h