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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 ...
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.
Tert-Butyl isocyanide; Butyl PBD; 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 ...
Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a high molecular weight additive, with low volatility. It is well suited to stabilising polyolefins against degradation caused by long term heat aging. [1] It is an approved food contact material in the US. [2]
As each phenol group contains only a single t-butyl group they are considered to have low steric hindrance and thus high activity. Arranging three of these around an isocyanurate core gives a compound with a sufficiently high boiling point that it is not volatilised out of the plastic during plastic extrusion and moulding (up to 320 °C in the case of PA).
The catalyst 1a is based on chiral 1,1′-Bi-2-naphthol (BINOL), the "R" indicating the chirality. "Boc" is tert-Butyloxycarbonyl protecting group . Catalytic asymmetric Strecker reaction can be effected using thiourea -derived catalysts . [ 7 ]