羟基保护基团及其稳定性
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羟基保护基团及其稳定性
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, RNH2NaOCH3 Electrophiles:RCOCl RCHO CH3I Others::CCl2Bu3SnH Reduction:H2 / Ni H2 / Rh Zn / HCl Na / NH3LiAlH4NaBH4
Oxidation:KMnO4OsO4CrO3 / Py RCOOOH I2, Br2, Cl2MnO2/ CH2Cl2
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 27-33, 708-711
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, RNH2NaOCH3 Electrophiles:RCOCl RCHO CH3I Others::CCl2Bu3SnH Reduction:H2 / Ni H2 / Rh Zn / HCl Na / NH3LiAlH4NaBH4
Oxidation:KMnO4OsO4CrO3 / Py RCOOOH I2, Br2, Cl2MnO2/ CH2Cl2
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: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
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 65-67, 708-711
Allyl ether
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 67-74, 708-711
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
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
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
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
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
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：
保护基在这些条件下稳定
保护基在这些条件下部分稳定或能反应
保护基在这些条件下不稳定