102831-44-7Relevant articles and documents
Studies toward the synthesis of caramboxin analogues
Oliveira Filho, Ronaldo E.,Higa, Vanessa M.,Omori, álvaro T.
, p. 528 - 540 (2019)
Intrigued by the recent discovery of caramboxin by Brazilian researchers, we present the results from our studies toward the racemic synthesis of caramboxin analogs through the ortho-carboxylation of 3,5-dimethoxy benzyl derivatives. Three different approaches were tested, and the route involving a Vilsmeier-Haack formylation followed by a Lindgren oxidation provide a potential intermediate for the synthesis of several caramboxin analogs.
Access to Enantiopure α-Hydrazino Acids for N-Amino Peptide Synthesis
Kang, Chang Won,Sarnowski, Matthew P.,Elbatrawi, Yassin M.,Del Valle, Juan R.
, p. 1833 - 1841 (2017)
Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydrazino acids derived from 19 out of the 20 canonical proteinogenic amino acids and demonstrate their use in the solid-phase synthesis of N-amino peptide derivatives.
β-Methyleneglutamic Acid and β-Methyleneglutamine
Paik, Yi Hyon,Dowd, Paul
, p. 2910 - 2913 (1986)
The novel β,γ-unsaturated amino acids β-methyleneglutamic acid (I) and β-methyleneglutamine (II) are readily prepared by addition of the protected aminomalonates III and VIII to the allenes ethyl buta-2,3-dienoate (IV) and cyanoallene (VII) followed by acid hydrolysis.Byproducts of the reaction are 4-amino-3-methylbut-2-enoic acid hydrochloride (VI) and 4-amino-3-methylbut-2-enamide hydrochloride (X).
Amine-Directed Palladium-Catalyzed C?H Halogenation of Phenylalanine Derivatives
Ville, Alexia,Annibaletto, Julien,Coufourier, Sébastien,Hoarau, Christophe,Tamion, Rodolphe,Journot, Guillaume,Schneider, Cédric,Brière, Jean-Fran?ois
supporting information, p. 13961 - 13965 (2021/09/14)
An efficient primary-amine-directed, palladium-catalyzed C?H halogenation (X=I, Br, Cl) of phenylalanine derivatives is reported on a range of quaternary amino acid (AA) derivatives thanks to suitable conditions employing trifluoroacetic acid as additive. The extension of this original native functionality-directed ortho-selective halogenation was even demonstrated with the more challenging native phenylalanine as tertiary AA.
Polybasic nitrogen heterocyclic non-natural chiral amino acid and synthesis method thereof
-
Paragraph 0063; 0065; 0066; 0093; 0095; 0096; 0123-0126, (2018/11/22)
The invention relates to a polybasic nitrogen heterocyclic non-natural chiral amino acid and a synthesis method thereof. The amino acid can be applied to molecule building for antibiotic synthesis. According to the synthesis method, 2-aminodiethyl malonate and halogenated alkanes carry out substitution reactions, cyclization reactions, and decarboxylation reactions, and the reaction products are split to obtain the polybasic nitrogen heterocyclic non-natural chiral amino acid. The provided novel synthesis method has the advantages of simple synthesis route, low cost, convenient operation, andeasiness for commercial production, the chiral purity of obtained products is high, and the application prospect is good.
