N,N'-Disuccinimidylcarbonate, A potential reagent in fine organic synthesis of reactive asymmetrical carbonates, used to protect amino groups from aminoacids for peptides synthesis

Carbamate-type amino protecting groups constitute by far the most important amino protecting groups and the benzyloxycarbonyl derivates are pre-eminent among these. One of the most important properties of the benzyloxycarbonyl group is the resistance it confers to the protected amino acids against racemization, and N-benzyloxycarbonyl amino-acids may be activated for peptide synthesis. N,N'-Disuccinimidylcarbonate (DSC) was prepared from N-hydroxysuccinimide and triphosgene (bis(trichloromethyl)carbonate), a solid compound possessing low-toxicity (successfully replacing phosgene). NN'-Disuccinimidylcarbonate is a suitable reagent in the synthesis of mixed primary-, secondary-, and tertiary-alkyl succinimidyl carbonates, these reactions occurring in one step, with high yields. The stability of these carbonates, together with the mild reaction conditions, make them preferred reagents in the protecting reactions by alkoxycarbonylation at nitrogen nucleophiles of amine- and aminoacid-types.