MOM-OR,Methoxymethyl ether, MOM ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 27-33, 708-711
THP-OR,Tetrahydropyranyl ether, THP ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 49-54, 708-711
t-Butyl ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py pH = 4, RT t-BuOK pH = 9, RT Others: pH = 12, RT DCC pH > 100°C SOCl2 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 RMgX RCHO H2 / Rh OsO4 RCuLi CH3I Zn / HCl CrO3 / Py Enolates Others: Na / NH3 RCOOOH NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 65-67, 708-711
Allyl ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 67-74, 708-711
Benzyl ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 76-86, 708-711
t-Butyldimethylsilyl ether, TBDMS ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 127-141, 708-711
t-Butyldiphenylsilyl ether, TBDPS ether H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 141-144, 708-711
Acetic acid ester, Acetate ester, Acetate H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999,
150-160, 712-715
Pivalic acid ester, Pivalate ester, Pivalate,Pv-OR H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 170-173, 712-715
Benzoic acid ester, Benzoate ester, Benzoate H2O: Bases: pH < 1, 100°C pH = 1, RT LDA NEt3, Py RMgX RCHO H2 / Rh OsO4 pH = 4, RT t-BuOK RCuLi CH3I Zn / HCl CrO3 / Py pH = 9, RT Others: Enolates Others: Na / NH3 RCOOOH pH = 12, RT DCC NH3, RNH2 :CCl2 LiAlH4 I2, Br2, Cl2 pH > 100°C SOCl2 NaOCH3 Bu3SnH NaBH4 MnO2 CH2Cl2 / 12, Nucleophiles: RLi Electrophiles: RCOCl Reduction: Oxidation: H2 / Ni KMnO4 T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 173-178, 712-715 图列颜色说明：
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