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Dr Sumanta Mondal
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All content following this page was uploaded by Dr Sumanta Mondal on 11 May 2018.
Protecting Groups
- 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.
- For example:
- The overall transformation required is ester to primary alcohol. This is a reduction of the ester, which requires
LiAlH4, but that will reduce the ketone as well which we don't want. We can avoid this problem if we "change" the
ketone to a different functional group first. Conceptually, this is like being able to put a cover (shown below) over
the ketone while we do the reduction, then removes the cover.
- In reality, the "molecular cover" is a protecting group. In this example, we protect the ketone as an acetal (which is
an ether and doesn't react with LiAlH4)
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 1
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
What is a protecting group?
- 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.
Note, however, that each protecting group incorporated in a multistep synthesis increases the synthesis
by two non-productive steps reducing the overall yield and efficiency of the synthesis.
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 2
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
- The ether protecting groups of alcohols can be grouped in the following categories:
(a) Silyl ether protecting groups
- These protections replace the acidic proton on an alcohol with an unreactive ether moiety.
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 3
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 4
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
- Because of resonance stabilization, the carbonyl of the ,-unsaturated ketone is less electrophilic and
therefore less reactive to nucleophiles compared to an isolated ketone.
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 5
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 6
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
ADVANCED ORGANIC CHEMISTRY – I (MPC 102T) UNIT- III: Protecting groups
Lecturer Notes_Dr. Sumanta Mondal_M. Pharm (Pharmaceutical Chemistry) _GITAM University Page | 7
E-mail: logonchemistry@gmail.com; phytochemistry@rediffmail.com
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