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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
Q

What ether forming alcohol protecting groups are cleaved with TMS-I? (3)

26
Q

What ether forming, alcohol protecting groups are cleaved with a hydrogenolitic cleave? (3)

A
  • Bn
  • PMB
  • BOM
27
Q

What ether protecting alcohol group is metal catalyzed cleaved?

28
Q

Alcohol protecting groups that form esters (3)

A
  • Acetyl
  • Benzoyl
  • Pivaloil
29
Q

How are alcohol, ester forming groups introduced? (2)

A
  • Acid chlorides
  • Anhydrides
30
Q

What bases are used to introduce alcohol ester forming protecting groups? (2)

A
  • Pyridine
  • Et3N
31
Q

Protecting groups for diols are:
(5)

A
  • Methylene
  • Acetinide
    Cyclo oentadiene
  • Cyclohexadene
  • Benzylidene
32
Q

What do diols from after protection?

A

Acetals or ketals

33
Q

What protecting groups is selective fir 1,3 diols?

A

Benzylidine

34
Q

What prot group is selective for 1,2 syndiols?

35
Q

How can thiols be protected? (3)

A
  • Acetamidometyls
  • Tritiyls
  • Thiolanes?
36
Q

Examples of acetamidomyls (4)

A
  • Acm
  • Tacm
    -Phacm
  • Alocam
37
Q

How are acm groups introduced? (2)

A
  • TFA
    -Triflic acid (stronger)
38
Q

How is Alocam cleaved?

A

Pd + Nu (metal catalized)

39
Q

For Acm, Tacm and Phacm, what are the possible cleavages? (2)

A
  • Oxidative with iodine
  • Hg, water and AcOh
40
Q

Examples of the trityl series (3)

A
  • Trt
  • Mtt
  • Mmt
41
Q

In which form are the protecting groups from trityl series introduced?

42
Q

What introduction conditions are needed for tritiyl prot groups?

43
Q

What are the trityl series cleavage conditions?

A

Acidic with TFA

44
Q

Which of the protecting groups used for alcohols are the same used for carboxilic acids? (3)

A
  • tBu
  • Bn
  • All
45
Q

Protecting groups for carboxilic acids (4)

A
  • Alkyl
  • tBu
  • Bn
  • Allyl
46
Q

What is the cleavage condition for Alkyl ester protecting group?

47
Q

What is the cleavage condition for tBu ester?

A

Acidic (TFA)

48
Q

What is the ceavage condition for bezyl ester?

A

Hydrogenolitic

49
Q

What is the cleavage condition for Allyl ester?

A

Metal catalized

50
Q

One way of protecting carboxilic acids is by means of a: ….. reaction

A

Steglich esterification

51
Q

What protecting groups can be used to protect terminal alkynes? (2)

A
  • TMS
  • Cobalt carbonyl complexes
52
Q

How is TMS cleaved from alkynes? (2)

A
  • TBAF
  • Acidic conditions
53
Q

How are cobalt carbonyl complexes removed from allkynes?

A

_ CAN (ceric amonium nitrate) = oxidative decomplexation

Chem (8 decks)

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