7433-32-1Relevant academic research and scientific papers
Synthesis method of (S)-2, 6-diamino-5-oxohexanoic acid
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Paragraph 0011, (2021/04/14)
The invention relates to a synthetic method of (S)-2, 6-diamino-5-oxohexanoic acid. The method mainly solves the technical problem of large-scale production of (S)-2, 6-diamino-5-oxohexanoic acid. The synthesis method comprises the following steps: reacting L-2-amino adipic acid with 9-fluorenylmethyl-N-succinimido carbonate in a mixed solution of water and acetone to generate a compound 1; under the catalysis of p-toluenesulfonic acid, reacting the compound 1 with paraformaldehyde in a toluene solution to generate a compound 2; reacting the compound 2 with di-tert-butyl dicarbonate, pyridine and ammonium carbonate in an ethyl acetate solution at room temperature to generate a compound 3; and reacting the compound 3 with lithium hydroxide in a mixed solution of ethanol and water to generate a target compound 4. As a derivative of (S)-2-amino adipic acid, (S)-2, 6-diamino-5-oxo hexanoic acid has become an important intermediate for the synthesis of alpha-amino adipic acid peptide.
Asymmetric synthesis of allylic secondary alcohols: Anewgeneral approach for the preparation of α-amino acids
Drummond, Lorna J.,Sutherland, Andrew
experimental part, p. 5349 - 5356 (2010/08/06)
A new general approach for the synthesis of optically active a-amino acids has been developed.The key steps involve a ruthenium catalysed cross-coupling reaction to give a range of α,β-unsaturated ketones, which were then reduced to allylic secondary alcohols in the presence of a chiral CBS oxazaborolidine.A thermal Overman rearrangement was used to prepare a series of allylic trichloroacetimidates and these were converted under standard conditions to the target α-amino acids in good overall yields.
Chemical Conversion of L-α,ο-Diamino Acids to L-ο-Carbamoyl-α-amino Acids by Ruthenium tetroxide Oxidation
Yoshifuji, Shigeyuki,Tanaka, Ken-ichi,Nitta, Yoshihiro
, p. 2994 - 3001 (2007/10/02)
Ruthenium tetroxide oxidation of N,C-protected derivatives of L-2,4-diaminobutyric acid, L-ornitine and L-lisine was carried out two-phase conditions and the corresponding imides, formed through the oxidation of the methylene adjacent to the ο-amino group, were obtained in good yields.Removal of the protecting groups from the products gave L-asparagine, L-glutamine and L-2-aminoadipic acid 6-amide, respectively.Thus the first chemical conversion of L-α,ο-diamino acids into the corresponding L-ο-carbamoyl-α-amino acids without racemization has been established.L-2-Aminoadipic acid 6-amide was further converted to L-2-aminoadipic acid by acid hydrolysis.This represents a convenient method for the synthesis of L-2-aminoadipic acid starting from L-lisine.Keywords - oxidation; ruthenium tetroxide; L-α-amino acid synthesis; N-protecting group; ruthenium tetroxide; L-α,ο-diamino acid; L-ο-carbamoiyl-α-amino acid; L-2-aminoadipicacid
PROPERTIES OF Nα,Nca-DI-TERT-BUTYLOXYCARBONYL-ω-CARBAMOYL-α-AMINO ACIDS AND DIRECT SYNTHESIS OF PROTECTED HOMOGLUTAMIC ACID DERIVATIVES
Sakura, Naoki,Hirose, Kyoko,Hashimoto, Tadashi
, p. 3506 - 3509 (2007/10/02)
The protected carboxamide function of Nα,Nca-di-tert-butyloxy-carbonyl-ω-carbamoyl-α-amino acids worked well with nucleophilic reagents.Applying this novel reactivity, we developed an efficient synthetic route to Nα-tert-butyloxycarbonylhomoglutamic acid and its derivatives, including Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester, from Nα,Nca-di-tert-butyloxycarbonylhomoglutamine.KEYWORDS - protected homoglutamic acid synthesis; Nca-tert-butyloxycarbonylated carboxamide; hydrolysis; selective deprotection; Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester; Nα-tert-butyloxycarbonylhomoglutamic acid α-tert-butyl ester; Nα-tert-butyloxycarbonylhomoglutamine; optical purity
