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Orthogonal protection of L-Tyrosine (Protecting groups are marked in blue, the amino acid is shown in black).(1) Fmoc-protected amino group, (2) benzyl ester protected carboxyl group and (3) tert-butyl ether protected phenolic hydroxyl group of Tyrosine.
tert-Butyloxycarbonyl protecting group. 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:
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
The tert-butyldiphenylsilyl group was first suggested as a protecting group by Hanessian and Lavallée in 1975. It was designed to supersede the use of Corey's tert-butyldimethylsilyl as a protecting group for alcohols:
Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R 1 R 2 R 3 Si−O−R 4 where R 4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis.
Tert-Butyl esters (14 P) N. N-tert-butyl-phenoxypropanolamines (24 P) ... Tert-Butyloxycarbonyl protecting group; Tert-Butylphosphaacetylene; Tert-Butylthiol;
General chemical structure of chloroformate esters. Chloroformates are a class of organic compounds with the formula ROC(O)Cl. They are formally esters of chloroformic acid. Most are colorless, volatile liquids that degrade in moist air. A simple example is methyl chloroformate, which is commercially available.
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. [1] Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc