Questions tagged [protecting-groups]

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15
votes
1answer
5k views

By what mechanism do acids deprotect primary silyl ethers?

Standard protocols report the selective deprotection of primary silyl ethers in the presence of secondary silyl ethers under acidic conditions, as exemplary shown in scheme 1, a reaction by Hartmann ...
6
votes
1answer
2k views

Can a benzyl ether be removed in the presence of an ester?

I'd like to deprotect a benzyl group for a Fráter–Seebach alkylation. Would it be possible to do this with a Birch reduction using Li/NH3 (or Na/NH3), without also reducing the ester carbonyl group? ...
5
votes
3answers
589 views

Effect of protecting group on diastereoselectivity of LiAlH4 reduction of α-hydroxyketones

In the reactions above, taken from Tetrahedron Lett. 1982, 23 (23), 2355–2358, the choice of protecting group on the α-hydroxyl group has a large influence on the diastereoselectivity of reduction. ...
4
votes
0answers
60 views

Synthesis of tripeptide using Merrifield peptide synthesis procedure - Inclusion of asparagine

I am supposed to synthesize tripeptide, $\mathrm{Ala-Asn-Phe}$, using Merrifield peptide synthesis procedure. Accordingly, I have done followings: Attached protected $\mathrm{Phe}$ as the first ...
1
vote
1answer
415 views

Can an ether be selectively hydrolysed in the presence of an ester?

What reaction, or protection/deprotection can be used to transform the ether group of a molecule that also has an ester compound into an alcohol while keeping the ester unchanged? For example: The ...