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The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group[1] (BOC group) is an acid -labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di- tert -butyl dicarbonate in the presence of a base such as sodium hydroxide:
Boc-Protected Amino-Groups in Multi-step Syntheses. SmCl 3 is an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive hydroxyl protecting groups such as Boc, THP, and TBDMS. Chemoselective deprotection is demonstrated through suitable examples.
Description: Amines can be protected as carbamate groups using reagents like Boc2O, CBzCl, and FMOC-Cl. These carbamates can be removed using acid (e.g. trifluoroacetic acid for Boc), catalytic hydrogenation (Pd-C, H2 for the CBz group) or basic conditions (piperidine for FMOC) respectively.
One of the most common carbamate protecting groups is the t -butyloxycarbonyl (Boc) protecting group. It can be removed with strong acid (trifluoroacetic acid) or heat. The carboxybenzyl (CBz) group has a benzyl group and can be removed using catalytic hydrogenation (Pd-C, H2)
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 .
What are protective groups? A protective group (also referred to as "protecting group") is a reversably formed derivative of an existing functional group in a molecule. The protective group is temporarily attached to decrease reactivity so that the protected functional group does not react under synthetic conditions to which the molecule is ...
The Boc group is the most used protection of amino groups for example in the synthesis of peptides, but let’s also discuss the phenylmethoxycarbonyl group (abbreviated carbobenzoxy or Cbz). The benzyl group is usually stable under acidic and basic conditions and is cleaved by catalytic hydrogenation with H 2 over Pd/C.
The Boc protecting group protects amines as less reactive carbamates in organic synthesis, and is deprotected with acid. N-Boc is a key topic during chemistry courses. Why? It nicely exemplifies important protecting group concepts and has an interesting deprotection mechanism.
The most common lactam nitrogen-protecting group for 3-pyrrolin-2-ones is the Boc (tert-butoxycarbonyl) group. The first introduction of the Boc group onto a 3-pyrrolin-2-one involved the parent 3-pyrrolin-2-one 1 (Scheme 2).
Protecting groups play a pivotal role in the synthesis of multifunctional targets and as amino functions often occur in this context, issues related to their protection become prominent. Primary amines are unique because they can accommodate two such groups.