Amino polyols are an important part of synthetically created amino acids. They are highly antibacterial and immunosuppressive and so are used in various antibiotics and antifungal products. This reaction shows one of the step necessary in creating the amino polyol.

Benzoyl chloride is added to the polyol to form a tribenzoate compound. In this reaction, the polyol has several R-O-H groups that act as weak nucleophiles. When the benzoyl-Cl bond breaks upon addition to the pyridine solvent, the benzoyl group acts as an electrophile. With the help of the DMAP (dimethylaminopyridine) catalyst in the reaction, the R-O-H group is deprotonated and the benzoyl group is added to the remaining R-O form the final tribenzoylated product. As seen above, the reaction has a yield of about 90%. The OTBS (t-buytldimethylsiloxy) groups do not participate in this reaction.

There is one hydroxyl group left on the molecule produced. All of the hydroxyl groups would be replaced by benzoyl groups if the reaction was not stopped after three groups had been added. To stop the reaction at this point, three equivalents of benzoyl chloride were used for every polyol.

There are four types of reactions:

Substitution Reactions

The reactions in which an atom or group of atoms in a molecule is replaced or substituted by different atoms or group of atoms are called substitution reaction. For example,

These reactions can be of two types:

Nucleophilic Substitution

In this type of substitution, atom or group of atoms in the molecule is replaced by a nucleophile. These can be either S_N1 (substitution, nucleophilic, unimolecular) or S_N2 (substitution, nucleophilic, bimolecular) type.
Read More