OAM-RC

Abstract

In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. The organic reactive carbonates are used especially as alkoxycarbonyl-type (carbamate) groups for protection of the amino function in amino acids. These protection groups are widely used in peptide synthesis because of their tendency to suppress racemisation of optically active centers. This paper presents the synthesis of new asymmetrical reactive carbonates with leaving group from the corresponding symmetrical carbonates and different type of alcohols, by an original procedure, as an alternative to the traditional method which employs toxic and dangerous reagents (phosgene and its chlorinated derivatives), as well as the applicability of these derivatives to the synthesis of bioactive compounds with many utilizations in pharmaceutics and food industries. The synthesis of asymmetrical primary-, secondary- and tertiary-alkyl phtalimidyl carbonates from N,N’-diphtamidylcarbonates (DPC) can be performed in one step reaction and with good yields. For the structure elucidations of final products was used the yield of these reactive carbonates depends on the alcohols reactivity, on the hindering factor and on the stability of the final product..

Keywords

Asymmetrical carbonates, Peptide synthesis, Phtalimidyl carbonates, Amino-protection groups.

Citation

A.-E. SEGNEANU, M. MILEA, I. GROZESCU, New series of asymmetrical carbonates used in peptide synthesis, Optoelectronics and Advanced Materials - Rapid Communications, 6, 5-6, May-June 2012, pp.656-659 (2012).

Submitted at: Jan. 14, 2012

Accepted at: June 6, 2012