Lecture 2 : Protecting groups

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10 Terms

1
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<p>alcohol protecting group using THP </p>

alcohol protecting group using THP

protect: DHP, PTsOH

deprotect: PTsOH, MeOH

2
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<p>alcohol protecting group using allyl group </p>

alcohol protecting group using allyl group

protect: allyl bromide, K2CO3

deprotect: Pd(PPh3)4

3
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<p>rank these in order of what deprotects first to last</p>

rank these in order of what deprotects first to last

OTMS, OTES, OTBDMS, OTIPS

4
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<p>Alcohols, silyl ethers </p>

Alcohols, silyl ethers

protect: OTMSCl,OTESCl, OTBDMSCl,OTIPSCl, NEt3

deprotect: TBAF

5
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<p>amines protecting group using phthalimide </p>

amines protecting group using phthalimide

protect: phthalic anhydride, NH4CO3

deprotect: H2NNH2

<p>protect: phthalic anhydride, NH4CO3</p><p>deprotect: H2NNH2</p>
6
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<p>amine protecting group using carbamate </p>

amine protecting group using carbamate

protect: di-tert-butyl dicarbonate, NAHCO3

deprotect: trifluoroacetic acid

<p>protect: di-tert-butyl dicarbonate, NAHCO3</p><p>deprotect: trifluoroacetic acid </p>
7
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<p>diols protecting group </p>

diols protecting group


protect: ketone, PTsOH

deprotect: PTsOH, H2O

8
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<p>carbonyl protecting group using diol </p>

carbonyl protecting group using diol

protect: diol, PTsOH

deprotect: PTsOH, H2O

<p>protect: diol, PTsOH</p><p>deprotect: PTsOH, H2O </p>
9
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<p>carbonyl protecting group using dithiol </p>

carbonyl protecting group using dithiol

protect: dithiol, BF3

deprotect: HgSO4, H2O

<p>protect: dithiol, BF3</p><p>deprotect: HgSO4, H2O </p>
10
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<p>carbonyl protecting groups</p>

carbonyl protecting groups

protect: dithiol, BF3

deprotect: Raney Ni

Clemensen: Zn(Hg), HCl, heat

Wolff Kishner: H2NNh2, KOH, heat

<p>protect: dithiol, BF3</p><p>deprotect: Raney Ni</p><p>Clemensen: Zn(Hg), HCl, heat </p><p>Wolff Kishner: H2NNh2, KOH, heat </p>