136620-75-2Relevant academic research and scientific papers
Methyl 2-[(tert-Butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate: Synthesis of Erythro (±) Isomer by Reduction and Threo (±) Isomer by Inversion Method
Giri Prasad, M.,Jonnalagadda, Sreekantha B.,Katari, Naresh Kumar,Kerru, Nagaraju,Rekulapally, Vijay Kumar,Vijaya Lakshmi, C.
, p. 2539 - 2545 (2022/01/22)
Abstract: We report an efficient protocol for synthesis of methyl 2-[(tert-butoxycarbonyl) amino]-3-hydroxy-3-phenylpropanoate (Erythro (±)) by simple reduction and methyl 2-[(tert-butoxycarbonyl) amino]-3-hydroxy-3-phenylpropanoate (Threo (±)) by inversi
Total Synthesis and Antimycobacterial Activity of Ohmyungsamycin A, Deoxyecumicin, and Ecumicin
Hawkins, Paige M. E.,Tran, Wendy,Nagalingam, Gayathri,Cheung, Chen-Yi,Giltrap, Andrew M.,Cook, Gregory M.,Britton, Warwick J.,Payne, Richard J.
, p. 15200 - 15205 (2020/10/23)
The ohmyungsamycin and ecumicin natural product families are structurally related cyclic depsipeptides that display potent antimycobacterial activity. Herein the total syntheses of ohmyungsamycin A, deoxyecumicin, and ecumicin are reported, together with the direct biological comparison of members of these natural product families against Mycobacterium tuberculosis (Mtb), the etiological agent of tuberculosis (TB). The synthesis of each of the natural products employed a solid-phase strategy to assemble the linear peptide precursor, involving a key on-resin esterification and an optional on-resin dimethylation step, before a final solution-phase macrolactamization between the non-proteinogenic N-methyl-4-methoxy-l-tryptophan amino acid and a bulky N-methyl-l-valine residue. The synthetic natural products possessed potent antimycobacterial activity against Mtb with MIC90’s ranging from 110–360 nm and retained activity against Mtb in Mtb-infected macrophages. Deoxyecumicin also exhibited rapid bactericidal killing against Mtb, sterilizing cultures after 21 days.
Total Synthesis of Ecumicin
Hawkins, Paige M. E.,Giltrap, Andrew M.,Nagalingam, Gayathri,Britton, Warwick J.,Payne, Richard J.
, p. 1019 - 1022 (2018/02/23)
The first total synthesis of the potent anti-mycobacterial cyclic depsipeptide natural product ecumicin is described. Synthesis was achieved via a solid-phase strategy, incorporating the synthetic non-proteinogenic amino acids N-methyl-4-methoxy-l-tryptophan and threo-β-hydroxy-l-phenylalanine into the growing linear peptide chain. The synthesis employed key on-resin esterification and dimethylation steps as well as a final macrolactamization between the unusual N-methyl-4-methoxy-l-tryptophan unit and a bulky N-methyl-l-valine residue. The synthetic natural product possessed potent antimycobacterial activity against the virulent H37Rv strain of Mycobacterium tuberculosis (MIC90 = 312 nM).
A process for producing an intermediate agonist GRK 3
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, (2016/10/09)
The present invention is directed to a process for preparing a compound of formula I-11 through multiple-step reactions.
Copper-catalyzed asymmetric hydroboration of α-dehydroamino acid derivatives: Facile synthesis of chiral β-hydroxy-α-amino acids
He, Zhi-Tao,Zhao, Yi-Shuang,Tian, Ping,Wang, Chuan-Chuan,Dong, Han-Qing,Lin, Guo-Qiang
supporting information, p. 1426 - 1429 (2014/04/03)
The Cu-catalyzed asymmetric conjugate hydroboration reaction of β-substituted α-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-β-boronate-α-amino acid derivatives with excellent combined yields (83-99%, dr ≈ 1:
CHIRAL FLUORINATING REAGENTS
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, (2014/05/24)
This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.
Asymmetric synthesis of 2,4,5-trisubstituted Δ2- thiazolines
Bengtsson, Christoffer,Nelander, Hanna,Almqvist, Fredrik
, p. 9916 - 9922 (2013/08/23)
Δ2-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to
PROCESS FOR MAKING BETA 3 ANGONISTS AND INTERMEDIATES
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Page/Page column 15; 17; 24-26, (2013/05/21)
The present invention is directed to a process for preparing a compound of formula I-11 through multiple-step reactions:.
Asymmetric synthesis of cis-2,5-disubstituted pyrrolidine, the core scaffold of β3-AR agonists
Xu, Feng,Chung, John Y. L.,Moore, Jeffery C.,Liu, Zhuqing,Yoshikawa, Naoki,Hoerrner, R. Scott,Lee, Jaemoon,Royzen, Maksim,Cleator, Ed,Gibson, Andrew G.,Dunn, Robert,Maloney, Kevin M.,Alam, Mahbub,Goodyear, Adrian,Lynch, Joseph,Yasuda, Nobuyashi,Devine, Paul N.
supporting information, p. 1342 - 1345 (2013/04/24)
A practical, enantioselective synthesis of cis-2,5-disubstituted pyrrolidine is described. Application of an enzymatic DKR reduction of a keto ester, which is easily accessed through a novel intramolecular N→C benzoyl migration, yields syn-1,2-amino alcoh
Enantioselective synthesis of anti-β-hydroxy-α-amido esters by asymmetric transfer hydrogenation in emulsions
Seashore-Ludlow, Brinton,Villo, Piret,Somfai, Peter
supporting information; experimental part, p. 7219 - 7223 (2012/07/13)
Herein, we present two methods for an asymmetric transfer hydrogenation through the dynamic kinetic resolution of α-amido-β-ketoesters. These procedures yield the corresponding anti-β-hydroxy-α-amido esters in good yields and with good diastereo- and enantioselectivities. First, the scope of the reduction of α-amido-β-ketoesters by using triethylammonium formate azeotrope is examined. Then, an emulsion technology with sodium formate is explored, which allows for broader substrate scope, faster reaction times, and lower catalyst loading. Furthermore, these reactions are operationally simple and can be set up in air.
