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Protecting Groups Flashcards

1
Q

Fmoc is for protecting…

A

Amines

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2
Q

Fmoc is cleaved with…

A

Piperidine (base)

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3
Q

After introduction Fmoc forms a…

A

Carbamate

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4
Q

Boc is for protecting…

A

Amines

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5
Q

Boc is cleaved with… (2 answers)

A

TFA, HCl

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6
Q

Cbz is for protecting…

A

Amines

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7
Q

After introduction Cbz forms a…

A

Carbamate

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8
Q

Cbz is cleaved with… (4 answers)

A
  • H2 with Pd/C (Palladium on Carbon) hydrogenolitic
  • Strongly acidic
  • NaNH3
  • TMS-I MeOH
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9
Q

Alloc forms …

A

Carbamate

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10
Q

After introduction Boc forms…

A

Carbamate

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11
Q

Alloc cleavage… (2 answers)

A
  • Metal catalyzed
  • Pd + nucleophile
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12
Q
A
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13
Q

Fmoc, Cbz, Alloc, Boc are introduced as.. (3 answers)

A
  • Anhydrides
  • Chlorides
  • Succinimides (just for Boc, Fmoc)
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14
Q

Reactivity of alcohols

A

Aromatic > 1> 2> 3

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15
Q

Silyl protecting groups are for

A

Alcohols

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16
Q

Silyl disadvantages

A

Movement in polyols

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17
Q

Alcohols can be protected as (3 answers)

A
  • Silylethers
  • Ethers
  • Esters
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18
Q

Form in which silyls are introduced…

A

X-Si-R3

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19
Q

Aromatic silyl protecting group

A

TBDPS

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20
Q

Usually silyl groups are stable against acids approx. to:

A

MW from bigger to smaller

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21
Q

Silyl groups covered (5 answers)

A
  • TMMS
  • TBDMS
  • TES
  • TIPS
    -TBDPS
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22
Q

Which ether protecting groups are specifically for phenols (2)

A
  • Methyl
  • tButyl
23
Q

Conditions for ether protecting groups introduction (2)

A
  • Basic conditions
  • Linked to a halogen
24
Q

Which groups protect alcohols by forming ethers? (9)

A
  • Methyl
  • Benzyl
  • MOM
  • tButyl
  • PMB
  • BOM
    -Alyl
    Tityl
    THP
25
What ether forming alcohol protecting groups are cleaved with TMS-I? (3)
- Me - Bn - PMB
26
What ether forming, alcohol protecting groups are cleaved with a hydrogenolitic cleave? (3)
- Bn - PMB - BOM
27
What ether protecting alcohol group is metal catalyzed cleaved?
Allyl
28
Alcohol protecting groups that form esters (3)
- Acetyl - Benzoyl - Pivaloil
29
How are alcohol, ester forming groups introduced? (2)
- Acid chlorides - Anhydrides
30
What bases are used to introduce alcohol ester forming protecting groups? (2)
- Pyridine - Et3N
31
Protecting groups for diols are: (5)
- Methylene - Acetinide Cyclo oentadiene - Cyclohexadene - Benzylidene
32
What do diols from after protection?
Acetals or ketals
33
What protecting groups is selective fir 1,3 diols?
Benzylidine
34
What prot group is selective for 1,2 syndiols?
Acetonide
35
How can thiols be protected? (3)
- Acetamidometyls - Tritiyls - Thiolanes?
36
Examples of acetamidomyls (4)
- Acm - Tacm -Phacm - Alocam
37
How are acm groups introduced? (2)
- TFA -Triflic acid (stronger)
38
How is Alocam cleaved?
Pd + Nu (metal catalized)
39
For Acm, Tacm and Phacm, what are the possible cleavages? (2)
- Oxidative with iodine - Hg, water and AcOh
40
Examples of the trityl series (3)
- Trt - Mtt - Mmt
41
In which form are the protecting groups from trityl series introduced?
As X-R
42
What introduction conditions are needed for tritiyl prot groups?
basic
43
What are the trityl series cleavage conditions?
Acidic with TFA
44
Which of the protecting groups used for alcohols are the same used for carboxilic acids? (3)
- tBu - Bn - All
45
Protecting groups for carboxilic acids (4)
- Alkyl - tBu - Bn - Allyl
46
What is the cleavage condition for Alkyl ester protecting group?
Basic
47
What is the cleavage condition for tBu ester?
Acidic (TFA)
48
What is the ceavage condition for bezyl ester?
Hydrogenolitic
49
What is the cleavage condition for Allyl ester?
Metal catalized
50
One way of protecting carboxilic acids is by means of a: ….. reaction
Steglich esterification
51
What protecting groups can be used to protect terminal alkynes? (2)
- TMS - Cobalt carbonyl complexes
52
How is TMS cleaved from alkynes? (2)
- TBAF - Acidic conditions
53
How are cobalt carbonyl complexes removed from allkynes?
_ CAN (ceric amonium nitrate) = oxidative decomplexation
54

Chem (8 decks)

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