5524-59-4Relevant academic research and scientific papers
Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
Lin, Zechao,Li, Jiahong,Huang, Qingfei,Huang, Qiuya,Wang, Qiwei,Tang, Lei,Gong, Deying,Yang, Jun,Zhu, Jin,Deng, Jingen
, p. 4419 - 4429 (2015/05/13)
A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).
Synthesis and evaluation of 6-Aza-2′-deoxyuridine monophosphate analogs as inhibitors of thymidylate synthases, and as substrates or inhibitors of thymidine monophosphate kinase in mycobacterium tuberculosis
Koegler, Martin,Busson, Roger,De Jonghe, Steven,Rozenski, Jef,Van Belle, Kristien,Louat, Thierry,Munier-Lehmann, Helne,Herdewijn, Piet
experimental part, p. 536 - 556 (2012/05/20)
A series of 5-substituted analogs of 6-aza-2′-deoxyuridine 5′-monophosphate, 6-aza-dUMP, has been synthesized and evaluated as potential inhibitors of the two mycobacterial thymidylate synthases (i.e., a flavin-dependent thymidylate synthase, ThyX, and a classical thymidylate synthase, ThyA). Replacement of C(6) of the natural substrate dUMP by a N-atom in 6-aza-dUMP 1a led to a derivative with weak ThyX inhibitory activity (33% inhibition at 50 μM). Introduction of alkyl and aryl groups at C(5) of 1a resulted in complete loss of inhibitory activity, whereas the attachment of a 3-(octanamido)prop-1-ynyl side chain in derivative 3 retained the weak level of mycobacterial ThyX inhibition (40% inhibition at 50 μM). None of the synthesized derivatives displayed any significant inhibitory activity against mycobacterial ThyA. The compounds have also been evaluated as potential inhibitors of mycobacterial thymidine monophosphate kinase (TMPKmt). None of the derivatives showed any significant TMPKmt inhibition. However, replacement of C(6) of the natural substrate (dTMP) by a N-atom furnished 6-aza-dTMP (1b), which still was recognized as a substrate by TMPKmt. Copyright
Synthesis of 3-alkylquinoxalin-2(1H)-ones via Grignard reaction
Kalinin,Mamedov
experimental part, p. 1098 - 1101 (2011/02/26)
A two-step procedure has been developed for the synthesis of 3-alkylquinoxalin-2(1H)-ones from o-phenylenediamine and ethyl 2-oxoalkanoates prepared by the Grignard reaction of diethyl oxalate with alkyl bromides. Analogous reaction with α,ω-dibromoalkanes instead of alkyl bromides leads to the formation of 3,3'-(alkane-α,ω-diyl)di[quinoxalin-2(1H) -ones].
Mild and Effective Removal of Dithioketal Protecting Groups by Triarylamine Cation Radicals as Homogeneous Electron Transfer Agents
Platen, Martin,Steckhan, Eberhard
, p. 1679 - 1694 (2007/10/02)
1,3-Dithianes 2 can effectively be converted into the parent carbonyl compounds 7 by a very mild oxidative procedure using tri-p-tolylammoniumyl (1a+.) or tris(4-bromophenyl)ammoniumyl (1b+.) as homogeneous electron transfer agents.The yields are equally good for the cleavage by stoichiometric amounts of the triarylammoniumyl hexachloroantimonates as well as for the indirect electrochemical procedure using catalytic amounts of the triarylamine together with electrochemical generation and regeneration of the cation radicals.In the case of 1,3-dithiolanes 3 the application of stoichiometric amounts of tris(4-bromophenyl)ammoniumyl hexa chloroantimonate is very effective while during the indirect electrochemical procedure the deposition of polymeric sulfur compounds onto the electrode surface has to be prevented by the use of a flowthrough cell.In all cases the conditions for the cleavage are so mild that hydroxy functions and double bonds are tolerated without problems.
AN EFFECTIVE AND MILD ELECTROCATALYTIC PROCEDURE FOR THE REMOVAL OF 1,3-DITHIANE PROTECTING GROUPS
Platen, Martin,Steckhan, Eberhard
, p. 511 - 514 (2007/10/02)
The 1,3-dithiane protecting group can effectively be removed by indirect electrochemical oxidation under extremely mild conditions, if catalytic amounts of tris(p-tolyl) amine are used as homogeneous electron transfer agents.
