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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 :
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
The tert-butyloxycarbonyl group is marked blue. Amines have a special importance in peptide synthesis, but are a quite potent nucleophile and also relatively strong bases. These characteristics imply that new protecting groups for amines are always under development. [47] Amine groups are primarily protected through acylation, typically as a ...
Tert-Butylamine; Butylated hydroxyanisole; Butylated hydroxytoluene; 4-tert-Butylbenzaldehyde; N-tert-Butylbenzenesulfinimidoyl chloride; Para-tert-Butylbenzoic acid; 4-tert-Butylcatechol; Tert-Butyldiphenylsilyl; Tert-Butylhydroquinone; Tert-Butyllithium; Tert-Butyloxycarbonyl protecting group; Tert-Butylphosphaacetylene; Tert-Butylthiol; N-t ...
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.
di-tert-butyl dicarbonate (H 3 C−) 3 C−C 2 O 5 −C(−CH 3) 3, also known as Boc anhydride. It is one of the oxocarbon anions, consisting solely of oxygen and carbon. The anion has the formula − O−C(=O)−O−C(=O)−O − or C 2 O 2− 5. Dicarbonate salts are apparently unstable at ambient conditions, but can be made under pressure ...
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In parallel, he worked on synthetic methods in peptide and protein chemistry such as the introduction of di-tert-butyl dicarbonate as a general and widely used reagent in peptide chemistry, [6] regioselective assembly of cystine-rich peptides, [7] and the synthesis of highly robust disulfide and diselenide scaffolds. [8]
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