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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 ...
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.
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 ...
Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) is a chemical compound composed of four sterically hindered phenols linked through a pentaerythritol core. It is used as primary antioxidant for stabilizing polymers, particularly polyethylene and polypropylene.
For this reason di-tert-butyl peroxide is commonly used as a radical initiator in organic synthesis and polymer chemistry. The decomposition reaction proceeds via the generation of methyl radicals. (CH 3) 3 COOC(CH 3) 3 → 2 (CH 3) 3 CO • (CH 3) 3 CO • → (CH 3) 2 CO + CH • 3 2 CH • 3 → C 2 H 6