常用氨基保护基的稳定性Stability-PGofAmine

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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

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

KMnO 4

OsO 4

CrO 3 / Py

RCOOOH

I 2, Br 2, Cl 2

MnO 2 / CH 2Cl 2

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

KMnO 4

OsO 4

CrO 3 / Py

RCOOOH

I 2, Br 2, Cl 2

MnO 2 / CH 2Cl 2

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

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

O O

O N

O N O F F

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

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

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

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

KMnO 4

OsO 4

CrO 3 / Py

RCOOOH

I 2, Br 2, Cl 2

MnO 2 / CH 2Cl 2

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

Ph Ph N

N S O O