1135150-41-2Relevant academic research and scientific papers
Synthesis and characterization of enantiomerically pure cis- and trans-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides as γ- homoacetylcholine mimetics and inhibitors of acetylcholinesterase
Clerc, Christian,Rueedi, Peter
scheme or table, p. 17 - 33 (2012/03/07)
The title compounds, the P(3)-axially and P(3)-equatorially substituted cis- and trans-configured 8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides (=8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphabicyclo[4.4.0]decane 3-oxides=2-fluorohexahydro-6-(phenylmethyl)-4H-1,3,2-dioxaphosphorino[5,4-c] pyridine 2-oxides) were prepared (ee>98%) and fully characterized (Schemes2 and 3). The absolute configurations were established from that of their precursors, the enantiomerically pure cis- and trans-1-benzyl-4- hydroxypiperidine-3-methanols which were unambiguously assigned. Being configuratively fixed and conformationally constrained phosphorus analogues of acetyl γ-homocholine (=3-(acetyloxy)-N,N,N-trimethylpropan-1-aminium), they are suitable probes for the investigation of molecular interactions with acetylcholinesterase. As determined by kinetic methods, all of the compounds are weak inhibitors of the enzyme. Copyright
The absolute configuration of the (+)- and (-)-cis- and (+)- and (-)-trans-1-benzyl-4-hydroxypiperidine-3-methanols: An unusual application of the1H-NMR-mosher method
Clerc, Christian,Matarazzo, Igor,Rueedi, Peter
scheme or table, p. 14 - 28 (2009/05/30)
The enantiomerically pure title compounds were prepared and the absolute configurations assigned by the high-field 1H-NMR application of the Mosher method on the bis-MTPA derivatives (MTPA - a-methoxy-a-(trifluoromethyl) benzeneacetic acid). Th
