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Org > Protecting groups > Flashcards

Protecting groups Flashcards

1
Q

Alcohol protecting groups

A 
Silyl
Alkyl ester
THP
Benzyl ethers (Bn and PMB)
Methyl ether
MOM ether
Alloc
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2
Q

Amine protecting groups

A 
Boc
Cbz
Benzyl
Sulfonyl
Fmoc
Phthalamide
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3
Q

Carboxyl protecting groups

A

Tert-butyl ester
Benzyl ester
Alloc

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4
Q

Carbonyl protecting groups

A

Acyclic acetal
Cyclic acetal
Thioacetal

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5
Q

Silyl group

A

Introduction: R3SiCl + base
Removal: TBAF (nBu4NF)

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6
Q

Alkyl ester

A

Introduction: Acid chloride/anhydride
Removal: Acid/base, H2O

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7
Q

THP acetal

A

Introduction: DHP, acid
Removal: acid, H2O

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8
Q

Benzyl (Bn) ether

A

Introduction: BnBr, base (NaH)
Removal: Pd/C, H2

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9
Q

PMB ether

A

Introduction: ArCH2Br, base (NaH)
Removal: DDQ or CAN

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10
Q

Methyl ether

A

Introduction: MeI, NaH
Removal: BBr3

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11
Q

MOM ether

A

Introduction: MeOCH2Cl, base
Removal: HCl

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12
Q

Alloc ether

A

Introduction: Alloc2O or Alloc-Cl
Removal: Pd(PPh3)4

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13
Q

Boc

A

Introduction: Boc2O, base
Removal: TFA

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14
Q

Cbz

A

Introduction: Cbz-Cl, base
Removal: Pd/C and H2 or HBr, AcOH

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15
Q

Benzyl

A

Introduction: BnBr, base OR PhCHO, NaBH4
Removal: Pd/C and H2

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16
Q

Tosyl

A

Introduction: Ts-Cl, base
Removal: HBr, AcOH

17
Q

Nosyl

A

Introduction: Ns-Cl, base
Removal: PhSH, Cs2CO3

18
Q

Fmoc

A

Introduction: FmocCl, base
Removal: piperidine

19
Q

Phthalamide

A

Introduction: … , base
Removal: H2N-NH2

20
Q

Tert-butyl ester

A

Introduction: 2-methylpropene, acid
Removal: TFA

21
Q

Benzyl ester

A

Introduction: BnOH, peptide coupling
Removal: Pd/C, H2

22
Q

Alloc ester

A

Introduction: allyl bromide, base
Removal: Pd(PPh3)4, amine nucleophile

23
Q

Acyclic acetal

A

Introduction: ROH, acid
Removal: H2O, acid

24
Q

Cyclic acetal

A

Introduction: OHCH2CH2OH, acid
Removal: acid, H2O

25
Q

Thioacetal

A

Introduction: HSCH2CH2CH2SH
Removal: IBX, H2O or HgO, H2O

Org (5 decks)

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