159090-52-5Relevant academic research and scientific papers
Preparation of the optically pure N-methyl amino ester method and product
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Paragraph 0059-0060, (2017/04/13)
The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.
Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: An easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine
Manna, Sudipta Kumar,Panda, Gautam
, p. 8318 - 8324 (2015/01/09)
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized within 5 min to 2 h in high yields from easily accessible (S)-amino acid derived chiral carbocations. The diastereoselective Friedel-Crafts reaction is promoted by a Lewis acid (AlCl3) offering trans-diastereoselectivity. The rate of the reaction and diastereoselectivity of the product are significantly influenced by steric hindrance of the amino acids substituents and aryl groups. The methodology can be applied for the synthesis of the enantiomerically enriched bioactive scaffold (3S,4R)-demethoxy-3-isopropyl diclofensine. This journal is
Highly enantioselective addition of diethylzinc to aldehydes catalyzed by novel chiral tert-amino alcohols
Zhang, Cong-Hai,Yan, Sheng-Jiao,Pan, Sheng-Qiang,Huang, Rong,Lin, Jun
experimental part, p. 869 - 873 (2010/10/04)
A series of novel chiral tert-amino alcohols 4a-h derived from enantiomerically pure phenylalanine were synthesized efficiently and used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc (diethylzinc-to-aldehyde addition). The use of 10 mol % of the amino alcohols led to the corresponding sec-alcohols with excellent enantioselectivities (up to 100% ee) and high yields.
'N-stereogenic quaternary ammonium salts' from L-amino acids: Synthesis, separation, and absolute configuration
Wu, Hua-Fang,Lin, Wen-Bin,Xia, Li-Zi,Luo, Ying-Gang,Chen, Xiao-Zhen,Li, Guo-You,Zhang, Guo-Lin,Pan, Xin-Fu
experimental part, p. 677 - 688 (2009/08/08)
Diastereoisomeric linear and cyclic 'N-chiral quaternary ammonium salts' (QASs) were efficiently synthesized from corresponding L-amino acids in high yields. The diastereoisomers of each pair of 'N-chiral QASs' were successfully separated. The absolute configurations of these QASs were determined predominately by X-ray single-crystal analysis. The 1H-NMR data of 'N-chiral QASs' provided characteristic information on the configuration of the N-chiral center. 'N-Chiral QASs' exemplified by [N(R)]-2a and [N(S)]-2a are stable in protic and aprotic solvents within a broad pH and temperature range.
A new inhibitor design strategy for carboxypeptidase A as exemplified by N-(2-Chloroethyl)-N-methylphenylalanine
Park, Jung Dae,Lee, Kyung Joo,Kim, Dong H.
, p. 237 - 243 (2007/10/03)
N-(2-Chloroethyl)-N-methylphenylalanine was designed and synthesized in an optically active form as a novel class of mechanism-based inactivator for carboxypeptidase A (CPA). It was anticipated that the chloroethylamino moiety of the CPA bound inhibitor undergoes an intramolecular SN2 reaction to generate a chemically reactive species (an aziridinium ion) which is expectedly subjected to a nucleophilic attack by the carboxylate of Glu-270, leading to covalent modification of the carboxylate. The irreversible nature of the inhibition of CPA by the inhibitor was supported by the kinetic data: the enzyme lost its enzymic activity in a time-dependent manner in the presence of the inhibitor and the inactivated CPA failed to regain the activity upon dialysis. Interestingly, the (R)-isomer that belongs to the D-series was more potent than its enantiomer.
Photoinduced electron transfer (PET) promoted oxidative activation of 1- (N-benzyl-N-methylglycyl)-(S)-prolinol: Development of novel strategies towards enantioselective syntheses of α-amino acids, their N-methyl derivatives and α-hydroxy acids employing
Pandey, Ganash,Das, Parthasarathi,Reddy, P. Yella
, p. 657 - 664 (2007/10/03)
PET activation of 1-(N-benzyl-N-methylglycyl)-(S)-prolinol (1) in dry acetonitrile, utilizing 1,4-dicyanonaphthalene (DCN) as a light-harvesting electron-acceptor and methyl viologen (MV++) as an electron-transfer mediator, leads to the formati
Synthesis and Utilisation of Chiral 3-N- Benzyl-N-methylaminoperhydropyrrolo-[2,1-c][1,4]oxazin-4-one as a Novel Precursor for the Enantioselective Synthesis of α-Amino Acids and Their N-Methyl Derivatives
Pandey, Ganesh,Das, Parthasarathi
, p. 634 - 639 (2007/10/03)
α-Amino acids and their N-methyl derivatives are synthesised in good optical purity by the nucleophilic alkylation of chiral 3-N-benzyl-N-methylaminoperhydropyrrolo[2,1-c][1,4]oxazin-4-one (1). The chiral auxiliary, L-prolinol, is isolated in recyclable f
