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Protected & Chiral Compounds

The protection of organic compounds plays an important role in multistep organic synthesis. Protection of functional groups is preferred to avoid unwanted reactions to obtain chemoselectivity in organic synthesis. The reduction of ester to alcohols using LiAlH4 in the presence of carbonyl groups is carried out by protecting the carbonyl group with acetal to avoid the interference during the reduction to get desired alcohol. The alcohols are protected by acetyl, benzoyl, benzyl, p-methoxybenzyl, silyl, or trityl groups. The common protecting groups used for amines are p-methoxybenzyloxycarbonyl, tert-butyloxycarbonyl, Tosyl, and p-methoxybenzyl. Acetals, ketals, dithianes are often used as protection for carbonyl groups. Similarly carboxyl groups are protected as methyl esters, benzyl esters, nitrobenzyl esters, p-methoxybenzyl esters, allyl esters, tert-butyl esters, and silyl esters.

Chiral compounds are non-superimposable on their mirror image and generally contain one asymmetric chiral center. The two non suprimposible mirror image forms of chiral compounds are called enantiomers. Chiral compounds exhibit optical activity. The enantiomers are classified as levorotary which rotates the plane polarised light towards the left and dextrorotatary which rotates the plane polarised light towards the right. The equimolar mixture of a chiral compound is called a racemic mixture. Many biological molecules like amino acids, carbohydrates, steroids, hormones, peptides, and enzymes are chiral compounds.


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