sodium periodate in tetrahydrofuran 24 h; Ambient temperature;

1: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 3: concd. NH4OH / acetone / 1.5 h 4: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 5: NH3, HCl / methanol / 0.08 h / Heating 6: NaBH4 / methanol; tetrahydrofuran / 0.5 h 7: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 5: concd. NH4OH / acetone / 1.5 h 6: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 7: NH3, HCl / methanol / 0.08 h / Heating 8: NaBH4 / methanol; tetrahydrofuran / 0.5 h 9: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 2: LiAlH4 / diethyl ether / 3 h / Ambient temperature 3: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 6: concd. NH4OH / acetone / 1.5 h 7: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 8: NH3, HCl / methanol / 0.08 h / Heating 9: NaBH4 / methanol; tetrahydrofuran / 0.5 h 10: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

2: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 3: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 4: LiAlH4 / diethyl ether / 3 h / Ambient temperature 5: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 8: concd. NH4OH / acetone / 1.5 h 9: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 10: NH3, HCl / methanol / 0.08 h / Heating 11: NaBH4 / methanol; tetrahydrofuran / 0.5 h 12: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 4: concd. NH4OH / acetone / 1.5 h 5: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 6: NH3, HCl / methanol / 0.08 h / Heating 7: NaBH4 / methanol; tetrahydrofuran / 0.5 h 8: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

2: concd. NH4OH / acetone / 1.5 h 3: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 4: NH3, HCl / methanol / 0.08 h / Heating 5: NaBH4 / methanol; tetrahydrofuran / 0.5 h 6: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: NH3, HCl / methanol / 0.08 h / Heating 2: NaBH4 / methanol; tetrahydrofuran / 0.5 h 3: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 2: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 3: LiAlH4 / diethyl ether / 3 h / Ambient temperature 4: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 7: concd. NH4OH / acetone / 1.5 h 8: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 9: NH3, HCl / methanol / 0.08 h / Heating 10: NaBH4 / methanol; tetrahydrofuran / 0.5 h 11: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: concd. NH4OH / acetone / 1.5 h 2: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 3: NH3, HCl / methanol / 0.08 h / Heating 4: NaBH4 / methanol; tetrahydrofuran / 0.5 h 5: aq. sodium periodate / tetrahydrofuran / 24 h / Ambient temperature View Scheme