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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:
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 ...
Pages in category "Tert-butyl compounds" The following 200 pages are in this category, out of approximately 203 total. This list may not reflect recent changes .
"Boc" is tert-Butyloxycarbonyl protecting group. Catalytic asymmetric Strecker reaction can be effected using thiourea-derived catalysts. [7] In 2012, a BINOL-derived catalyst was employed to generate chiral cyanide anion (see figure). [8]
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.
Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.
Mono-BOC-cystamine (mono BOC protected cystamine) is a tert-butyloxycarbonyl (BOC) derivative of cystamine used as crosslinker in biotechnology and molecular biology applications. [1] This compound was originally reported by Hansen et al .