124206-66-2Relevant academic research and scientific papers
Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4- tetrahydroisoquinoline derivatives
Orden, Alejandro A.,Schrittwieser, Joerg H.,Resch, Verena,Mutti, Francesco G.,Kroutil, Wolfgang
, p. 744 - 749 (2013/07/25)
A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenyl
Synthesis of mercapto-(+)-methamphetamine haptens and their use for obtaining improved epitope density on (+)-methamphetamine conjugate vaccines
Carroll, F. Ivy,Blough, Bruce E.,Pidaparthi, Ramakrishna R.,Abraham, Philip,Gong, Paul K.,Deng, Liu,Huang, Xiaodong,Gunnell, Melinda,Lay, Jackson O.,Peterson, Eric C.,Owens, S. Michael
experimental part, p. 5221 - 5228 (2011/10/02)
This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (KD = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.
ASYMMETRIC SYNTHESIS IX: PREPARATION OF CHIRAL α-SUBSTITUTED PHENETHYLAMINES
Marco, Jose L.,Royer, Jacques,Husson, Henri-Philippe
, p. 669 - 676 (2007/10/02)
(S)-N-methyl-α-methyl-phenethylamines 5a-d were obtained in 56-62 percent e.e. from chiral synthon (-)-N-cyanomethyl-4-phenyl-1,3-oxazolidine-1.
α-Amino Acids as Chiral Educts for Asymmetric Products. Amino Acylation with N-Acylamino Acids
Buckley, Thomas F.,Rapoport, Henry
, p. 6157 - 6163 (2007/10/02)
α-N-Acylamino acids have been developed as useful reagents for the preparation of optically pure α-aminoalkylaryl ketones.Protection of the amino group as either the ethoxycarbonyl or benzenesulfonyl derivative allows alanine to serve as an effective educt for the chirally specific synthesis of a variety of structures containing the phenylethylamine backbone.Benzene undergoes Friedel-Crafts acylation with the N-acylalanine acid chloride.Catalyst complexation with oxagenated aromatics, however, prohibits acylation of aryl ethers.An arylmetallo reaction scheme overcomes this problem and also affords regiospecificity not attainable in conventional acylations.As examples, optically pure ephedrines and amphetamines were directly synthesized without recourse to resolution since the chirality of the amino acid educt was entirely conserved throughout the process.
