73872-72-7Relevant academic research and scientific papers
Enantioselective synthesis of diamino dicarboxylic acids
Hiebl, Johann,Kollmann, Hermann,Rovenszky, Franz,Winkler, Karin
, p. 1947 - 1952 (2007/10/03)
The preparation of alkyl diamino dicarboxylic acids with high optical purity (100% ee, >98.5% de) and high yields based on asymmetric catalytic hydrogenation is described. The required prochiral precursors are prepared from dialdehydes and Z-, Boc-, and acetyl-protected phosphonoglycines. Aqueous solutions of glyoxal, succinic dialdehyde, and glutaric dialdehyde were used to prepare the diunsaturated precursors for 2,5-diaminoadipic acid (DAA), 2,7-diaminosuberic acid (DAS), and 2,8-diaminoazelaic acid (DAZ). Z- Protected dimethyl esters of DAA, DAS, and DAZ were obtained by hydrogenation of the corresponding prochiral starting materials with [(COD)Rh(S,S)- EtDuPHOS]OTf.
A detailed investigation of the preparation of 2,7-diaminosuberic acid and 2,5-diaminoadipic acid derivatives using Kolbe electrolysis
Hiebl, Johann,Blanka, Michael,Guttman, Andras,Kollmann, Hermann,Leitner, Kornelia,Mayrhofer, Guenter,Rovenszky, Franz,Winkler, Karin
, p. 2059 - 2074 (2007/10/03)
The yield of protected 2,7-diaminosuberic acid (DAS) prepared by Kolbe reaction of N-protected α-glutamic acid esters is dependent on solvent, temperature, concentration of carboxylate onion, and protecting groups. The highest yield of protected L,L-2,7-diaminosuberic acid is obtained with Boc-Glu-OMe as starting material using MeOH/pyridine/NaOMe as electrolyte.
Efficient synthesis of differentially protected (S,S)-2,7- diaminooctanedioic acid, the dicarba analogue of cystine
Lange, Meinolf,Fischer, Peter M.
, p. 2053 - 2061 (2007/10/03)
Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carb
