Functional Groups:
Protecting group is stable under these conditions
Protecting group is moderately stable / might react
Protecting group is labile
Carboxyl Protecting Groups Stability
Methyl ester | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 383-387, 728-731.
t-Butyl ester | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 404-408, 728-731.
Benzyl ester | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 415-419, 728-731.
S-t-Butyl ester | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 431-433, 728-731.
2-Alkyl-1,3-oxazoline | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 433-435, 728-731.