What is the Boc group used to protect?
tert-butyloxycarbonyl
Amine protection The tert-butyloxycarbonyl (Boc) group is used as a protecting group for amines in organic synthesis.
How does a Boc group protect an amine?
The protection of amines with tert-butyloxycarbonyl (Boc) group is a widely used reaction in organic synthesis because of its inertness toward catalytic hydrogenolysis and resistance toward hydrolysis under most basic conditions and nucleophilic reagents [3].
Why is BOC used?
tert-Butyloxycarbonyl (Boc) is a protecting group often used in the synthesis of organic compounds. Boc is specifically used to protect amine in the solid phase synthesis of peptides (Green, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, Wiley-Interscience: New York, 1999, pp 518-525, 736-739).
For what purpose is BOC used?
What is BOC in organic chemistry?
What are good protecting groups?
Common protecting groups
- Acetyl (Ac) – Removed by acid or base (see Acetoxy group).
- Benzoyl (Bz) – Removed by acid or base, more stable than Ac group.
- Benzyl (Bn) – Removed by hydrogenolysis.
- β-Methoxyethoxymethyl ether (MEM) – Removed by acid.
How do you do BOC protection?
The formation of Boc-protected amines and amino acids is conducted under either aqueous or anhydrous conditions, by reaction with a base and the anhydride Boc2O. Active esters and other derivatives such as Boc-ONH2 and Boc-N3 can also be used. The Boc group is stable towards most nucleophiles and bases.
Is BOC water soluble?
Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis….Di-tert-butyl dicarbonate.
Names | |
---|---|
Boiling point | 56 to 57 °C (133 to 135 °F; 329 to 330 K) (0.5 mmHg) |
Solubility in water | Insoluble |
Solubility in other solvents | Soluble in most organic solvents |
What are the qualities one looks for in a protecting group?
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.
What is the mechanism of Boc deprotection?
Boc Deprotection Mechanism – TF . 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.
Which is the best protection group for BOC?
The Boc group is stable towards most nucleophiles and bases. Therefore, an orthogonal protection strategy using a base-labile protection group such as Fmoc is possible. tert -Butyl carbamates are cleaved under anhydrous acidic conditions with the production of tert -butyl cations.
How is a BOC protected amine catalyzed?
A nickel boride catalyzed reduction of nitriles allows the preparation of Boc protected amines. The catalytic use of nickel(II) chloride in combination with excess sodium borohydride is environmental benign and tolerates air and moisture. Although the yield is sometimes moderate,…
How is the tert butoxycarbonyl group used in catalytic deprotection?
These initial studies dealt with the catalytic deprotection of poly ( ( tert-butoxycarbonyloxy)styrene) (TBS) in which the thermally stable, acid-labile tert-butoxycarbonyl group is used to mask the hydroxyl functionality of poly (vinylphenol).