Presentation On

PROTECTING GROUPS
What is protecting groups?
Any chemical entity that is temporarily reacted with a functional
group so as to protect it from a subsequent reaction.

FG= Functional group

PG= Protecting group
Protecting groups in organic
synthesis
Choosing a suitable protecting
group
When we have to choose a suitable protecting group,
the following features must be considered:
Cheap & commercially available
Simple to put in high yield
Stable to reaction conditions
Easy to remove in high yield
Protection of Alcohols
Protecting groups for alcohols:
Acetals or ketals
Ether
Ester
Acetals or Ketals
 Acelals or ketals not only serve as useful protecting groups
for aldehydes and ketones but they also find widespread
use in the protection of alcohols.
 Commonly used ketals include Tetrahydropyranyl (THP)
derivatives, methoxyethoxymethyl (MEM) derivative
and methoxymethyl (MOM) derivative.
 Acetals / ketals are simply removed by treatment with
aqueous acid.
 Ether as protecting group
Alcohols may be simply converted to ethers by nucleophilic attack
on a suitable alkyl halide. Ethers are stable to basic and mildly
acidic conditions; they do not react with oxidizing / reducing
agents and are inert to organo-metallic reagents. Ex:
Benzyl ether which are converted to alcohols under neutral
conditions by catalytic hydrogenolysis.
Esters as protecting group
Trichloroacetate esters [Cl3CCOOR]:

Pivoloate ester [Me3CCOOR]:

Protection of Amines
The basic problem of peptide synthesis is one of
protecting the amino group. In bringing about
interaction between the carboxyl group of one
amino acid and the amino group of a different
amino acid, one must prevent interaction
between the carboxyl group and the amino group
of the same amino acid.
 Protecting groups for Amines
Carbamates as protecting groups for amines:
9-Fluorenylmethyl carbamate (Fmoc or 9-fluorenylmethyloxycarbonyl):
9-fluorenylmthyloxycarbonyl protection is used for an alcohol or amine
and it is carried out with an Fmoc-X reagent (X=Cl or N3) in the
presence of pyridine or NaHCO3.
Formation:
Protecting groups for Amines
(Cont.)
Cleavage:
Thank You
Presented & created by:
Md. Rasheduzzman Biswas Md. Azizul Islam
ID: 17161001 ID: 17161006
Israt Jahan Ema Md. Khairul Bashar
ID: 17161002 ID: 17161010