Why is Boc a good protecting group?
Why is Boc a good protecting group?
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. Scavengers such as thiophenol may prevent nucleophilic substrates from being alkylated.
How do you remove acetyl protecting group?
Acetyl (Ac) group is common in oligonucleotide synthesis for protection of N4 in cytosine and N6 in adenine nucleic bases and is removed by treatment with a base, most often, with aqueous or gaseous ammonia or methylamine.
How do I get rid of mom protecting group?
Since the MOM group is an acetal, it can be cleaved by acid hydrolysis. In general, it can be removed by boiling in methyl alcohol in presence of trace of conc. HCl. Other methods using variety of acids in organic solvents can also be employed to remove the protection.
How are protecting groups removed?
How do you protect from BOC?
Protection of the amine can also be accomplished in acetonitrile solution using 4-dimethylaminopyridine (DMAP) as the base. Removal of the BOC in amino acids can be accomplished with strong acids such as trifluoroacetic acid in dichloromethane, or with HCl in methanol.
What is p-methoxybenzyl (PMB)?
General Characteristics –p-Methoxybenzyl (PMB or MPM) group can be protected or deprotected under the same conditions as benzyl group. It can also be deprotected under mildly oxidizing conditions using DDQ (dichlorodicyanobenzoquinone) or strongly acidic conditions.
What is PMB protective group in organic chemistry?
p-Methoxybenzyl (PMB) Protective Group. –p-Methoxybenzyl (PMB or MPM) group can be protected or deprotected under the same conditions as benzyl group. It can also be deprotected under mildly oxidizing conditions using DDQ (dichlorodicyanobenzoquinone) or strongly acidic conditions.
Is there a group orthogonal to p -methoxy benzyl?
Gregory B. Dudley of Florida State University has developed ( Tetrahedron Lett. 2005, 46, 3283. DOI: 10.1016/j.tetlet.2005.03.110 ) a group that is orthogonal to p -methoxy benzyl, based on a p -siletanyl group (PSB). Mild conditions convert 3 to the p -hydroxybenzyl ether, which is removed very quickly with FeCl 3.
What is the formula for BOC protected amine?
MnO 2 / CH 2 Cl 2. General. 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 Boc 2 O. Active esters and other derivatives such as Boc-ONH 2 and Boc-N 3 can also be used. The Boc group is stable towards most nucleophiles and bases.
