[中学教育]羟基保护基团及其稳定性

[中学教育]羟基保护基团及其稳定性 羟基保护基团及其稳定性 MOM-OR,Methoxymethyl ether, MOM ether pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 49-54, 708-711 t-Butyl ether pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32 Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 65-67, 708-711 Allyl ether pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 67-74, 708-711 Benzyl ether pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 / MnO2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 MnO / 2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 MnO / 2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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 pH > 12, HO: pH < 1, 100?C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT 2100?C Bases: LDA NEt, Py t-BuOK Others: DCC SOCl 32Nucleophiles: RLi RMgX RCuLi Enolates NH, RNH NaOCH 323Electrophiles: RCOCl RCHO CHI Others: :CCl BuSnH 323Reduction: H / Ni H / Rh Zn / HCl Na / NH LiAlH NaBH 22344 MnO / 2Oxidation: KMnO OsO CrO / Py RCOOOH I, Br, Cl 443222CHCl 22T. 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