Do protecting groups work on esters?

Do protecting groups work on esters?

When a reduction of an ester is required in the presence of a carbonyl, the attack of the hydride on the carbonyl has to be prevented. For example, the carbonyl is converted into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl.

How thiols are protected?

The most commonly used photoprotection groups for thiols are phenacyl, benzoinyl, o-nitrobenzyl groups and coumarinyl groups. These groups are generally also useful for the protection of other functional groups, but they will be discussed here for thiols in particular.

Why are silyl ethers good protecting groups for alcohols?

This is why silyl ethers make good protecting groups. They are exceptionally stable in base solution. In acid solution, they are easily removed to regenerate the original alcohol. You can even avoid strong acid, because F⁻ ions also react with the silane and regenerate the alcohol.

How do you know when to use a protecting group?

1. Protecting groups are used in synthesis to temporarily mask the characteristic chemistry of a functional group because it interferes with another reaction.
2. A good protecting group should be easy to put on, easy to remove and in high yielding reactions, and inert to the conditions of the reaction required.

Which group is used to protect carboxylic acids?

Protection of carboxylic acids: Methyl esters – Removed by acid or base. Benzyl esters – Removed by hydrogenolysis. tert-Butyl esters – Removed by acid, base and some reductants.

What is acetal group?

What is an acetal functional group? A functional group in which carbon is attached by single bonds to two ether oxygen and two carbons (or hydrogens). A thioacetal has two sulfur atoms in place of an acetal’s two oxygen atoms.

What is the use of FMOC protecting group in organic synthesis?

Fmoc protection has found significant use in solid phase peptide synthesis (SPPS), because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin.

How is benzoyl protecting group removed?

Benzoyl (Bz) group is common in oligonucleotide synthesis for protection of N4 in cytosine and N6 in adenine nucleic bases and is removed by treatment with a base, most often with aqueous or gaseous ammonia or methylamine. Bz is too stable to be readily removed from aliphatic amides.

How can we protect hydroxyl group?

In the case of alcohols the hydroxyl group may be protected by formation of an ether, an ester, or an acetal.