常用氨基保护基的稳定性Stability-PGofAmine

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Stability: Protecting Groups of Amine (1)

l 9-Fluorenylmethyl carbamate, Fmoc amino, Fmoc amine, Fmoc amide:

H2O: pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2/CH2Cl2

OONBases:

Nucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l t-Butyl carbamate, Boc amine, Boc amino, Boc amide:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

OONNucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Benzyl carbamate, Cbz-NR2 / Z-NR2:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

OONNucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Acetamide, Ac-NR2:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

ONNucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Trifluoroacetamide:

H2O: pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

OFFNFBases:

Nucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

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Stability: Protecting Groups of Amine (2)

l Phthalimide:

H2O: pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

ONROBases:

Nucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Benzylamine, Bn-NR2:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

NNucleophiles:

RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Triphenylmethylamine (Tritylamine), Tr-NR2:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

PhPhPhNNucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l Benzylideneamine:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

NNucleophiles: RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4

l p-Toluenesulfonamide, Tosylamide, Ts-NR2:

H2O:

Bases:

pH < 1, 100°C pH = 1, RT

LDA NEt3, Py

RMgX

RCHO

H2 / Rh

OsO4

pH = 4, RT

t-BuOK

RCuLi

CH3I

Zn / HCl

CrO3 / Py

pH = 9, RT

Others:

Enolates

Others:

Na / NH3

RCOOOH

pH = 12, RT

DCC

NH3, RNH2

:CCl2

LiAlH4

I2, Br2, Cl2

pH > 12, 100°C

SOCl2

NaOCH3

Bu3SnH

NaBH4

MnO2 / CH2Cl2

OSNONucleophiles:

RLi

Electrophiles: RCOCl

Reduction:

Oxidation:

H2 / Ni

KMnO4