A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis.
Why are protecting groups used in organic synthesis?
Protecting groups are used in synthesis to temporarily mask the characteristic chemistry of a functional group because it interferes with another reaction. 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.
How can we protect primary alcohols?
Silicon ethers are the most commonly used alcohol protecting groups. The O-Si bond formed is strong and less reactive to strong bases compared to the O-H bond in the parent alcohol.
How do I get rid of a protecting group?
The silyl ether protecting group can be removed by reaction with an aqueous acid or the fluoride ion.
How can we protect the OH group of alcohol?
In the case of alcohols the hydroxyl group may be protected by formation of an ether, an ester, or an acetal.
Can be used as protecting group for protection of chiral alcohol?
Ethers can also be used for alcohol protection. Two common ether-based protecting groups are THP- (tetrahydropyranyl-) and MOM- (methoxymethyl-).
Why is FMOC a good protecting group?
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. A typical SPPS Fmoc deprotection is performed with a 20% solution of piperidine in N,N-dimethylformamide.
Are protective groups needed for organorganic synthesis?
Organic synthesis has not yet matured to the point where protective groups are not needed for the synthesis of natural and unnatural products; thus, the develop- ment of new methods for functional group protection and deprotection conti- nues.
What is a good protecting group in organic chemistry?
A protecting group (PG) is a molecular framework that is introduced onto a specific functional group (FG) in a poly-functional molecule to block its reactivity under reaction conditions needed to make modifications elsewhere in the molecule. 1:56 PM 4. Qualities of a Good Protecting Group in Organic Synthesis.
What is an orthogonal set of protective groups?
K. C. Nicolaou and co-workers, Angew. Chem. Int. Ed. 1998, 37, 2708. Protective Groups: Orthogonal Sets of Protecting Groups Orthogonal Set = a groups of protecting groups whose removal is accomplished in any order with reagents and conditions that do not affect protecting groups in any other orthogonal set.
