常用氨基保护基的稳定性Stability-PGofAmine
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l
9-Fluorenylmethyl carbamate, Fmoc amino, Fmoc amine, Fmoc amide:
H 2O:
pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2/CH 2Cl 2
l
t -Butyl carbamate, Boc amine, Boc amino, Boc amide:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
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Benzyl carbamate, Cbz-NR 2 / Z-NR 2:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
l
Acetamide, Ac-NR 2:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
l Trifluoroacetamide:
H 2O:
pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH O
N
O O
N
O O
N
O N
O N O F F
F
l
Phthalimide:
H 2O:
pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
l Benzylamine, Bn-NR 2:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
l Triphenylmethylamine (Tritylamine), Tr-NR 2:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
l Benzylideneamine :
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH Reduction: H 2 / Ni H 2 / Rh Zn / HCl Na / NH 3 LiAlH 4 NaBH 4 Oxidation:
KMnO 4
OsO 4
CrO 3 / Py
RCOOOH
I 2, Br 2, Cl 2
MnO 2 / CH 2Cl 2
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p -Toluenesulfonamide, Tosylamide, Ts-NR 2:
H 2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C Bases:
LDA
NEt 3, Py t-BuOK Others: DCC SOCl 2 Nucleophiles: RLi RMgX RCuLi Enolates NH 3, RNH 2 NaOCH 3 Electrophiles: RCOCl RCHO CH 3I Others: :CCl 2 Bu 3SnH N O O
R N
N
Ph
Ph Ph N
N S O O。