74124-83-7Relevant academic research and scientific papers
New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors
Candelon, Nicolas,Shinkaruk, Svitlana,Bennetau, Bernard,Bennetau-Pelissero, Catherine,Dumartin, Marie-Laurence,Degueil, Marie,Babin, Pierre
experimental part, p. 2463 - 2469 (2010/06/14)
An original synthetic route to asymmetrically substituted methoxypyrazine (MP) derivatives is described. The first step of the synthesis is achieved by condensation of 1,2-aminoalcohols with Boc-protected aliphatic aminoacids followed by cycloimine formation and aromatization via chlorination. Introduction of methoxy group was then achieved by alkoxy-de-halogenation. The use of primary or secondary aminopropanol enabled the direct and selective introduction of methyl group, in 5- or 6-position, which can be easily functionalized. Aromatization of diketopiperazine, prepared from l-valine and l-glutamic acid dimethyl ester, made possible a direct introduction of a functionalized alkyl chain. These reactions are also suitable for the synthesis of naturally-occurring MPs such as wine flavor components and biologically active substances.
LE CHLOROFORMIATE D'ISOPROPENYLE (IPCF) EN CHIMIE DES AMINO-ACIDES ET DES PEPTIDES - III SYNTHESE D'ESTERS ACTIFS D'AMINO ACIDES N-PROTEGES
Jaouadi, M.,Selve, C.,Dormoy, J. R.,Castro, B.,Martinez, J.
, p. 1721 - 1722 (2007/10/02)
Isopropenyl chloroformate (IPCF) was used for preparation of mixed carbonates (Aryl and isopropenyl) which are very suitable reagents for active ester synthesis of amino acid derivatives (Boc derivatives in particular).
