What is an orthogonal protecting group?
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure without affecting the others. Due to this effect the quantum yield for deprotection of the right-side ester group is reduced and it stays intact.
What is a Nosyl group?
A group that is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction.
What are the amine protecting groups?
Carbamates are useful as protecting groups for amines, and the most commonly employed are -Boc, -Cbz, and -Fmoc. The -Cbz (carboxybenzyl) protecting group was first used by Max Bergmann and Leonidas Zervas in 1932 for the synthesis of peptides, and is sometimes abbreviated “-Z” in honor of Zervas.
What is amino protecting group?
The most common α-amino-protecting groups for solid-phase peptide synthesis (SPPS) are the 9-fluorenylmethoxycarbonyl (Fmoc) and the tert-butyloxycarbonyl (Boc) groups, used in the Fmoc/tert-butyl (tBu) and Boc/benzyl (Bn) strategies respectively.
What is a good 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.
How do I remove SEM protecting groups?
SEM groups can be removed from protected heterocycles or nitrogen containing compounds using hydrochloric acid under refluxing conditions or at elevated temperature, while SEM protecting groups on nucleosides have been removed using tin tetrachloride at low temperature.
What is TsO organic chemistry?
Tosylate (toluenesulfonate; p-toluenesulfonate): An ester or salt of p-toluenesulfonic acid. p-Toluenesulfonate anion (p-toluenesulfonate ion; TsO-)
What makes a good protecting group?
What are the general characteristics of a good protecting group?
How do I get rid of protecting groups?
The silyl ether protecting group can be removed by reaction with an aqueous acid or the fluoride ion. By utilizing a protecting group a Grignad reagent can be formed and reacted on a halo alcohol.
Is Otms a good leaving group?
Chlorides, bromides, and tosylate / mesylate groups are excellent leaving groups in nucleophilic substitution reactions, due to resonance delocalization of the developing negative charge on the leaving oxygen.
What is the SEM protecting group?
The trimethylsilylethoxymethyl (SEM) group is frequently used for the protection of alcohols and amines for the synthesis of carbohydrates and natural products. The trimethylsilylethoxymethyl group easily survives under bromination, basic hydrolysis, oxidation and other harsh conditions.
How are sulfonyl protective groups ( NS ) deprotected?
The deprotection of sulfonyl groups is relatively difficult. When it has to be done under mild conditions, one-electron reductive conditions (e.g. Mg/MeOH) can be used. Ns group is synthetically valuable as it can be deprotected by nucleophilic addition of a thiolate ( the Fukuyama amine synthesis ).
Which is more removable NS Group or TS Group?
Sulfonamides of primary amines have a sufficiently acidic proton, which can be used to synthesize secondary amines under the Mitsunobu or other alkylation conditions. For this purpose, more easily removable Ns group is used more frequently than Ts group ( the Fukuyama amine synthesis ).
Which is the best deprotection agent for nosyl group?
The most common deprotection conditions use either thiophenol or thioglycolic acid (HSCH2 CO 2 H) in the presence of base. An advantage of thioglycolic acid is the fact that the cleavage side product, nitrophenylthioacetic acid, can be washed away from the product with aqueous NaHCO 3.
Can a BOC protected group be deprotected?
Another opportunity is to build a larger molecule from subunits in which similar or identical functional groups have been differently protected beforehand. For example, a Boc-protected amino group can be deprotected in acidic media, whereas a Fmoc-protected amino group can be deprotected under basic conditions.