Determination of the absolute configuration of an unexpectedly stable N-silylated isomer isolated en route to the trinem antibiotic GV129606 |
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| Institution: | 1. Department of Materials Science and Engineering, The Ohio State University, 1248 Arthur E. Adams Dr, Columbus, OH, USA;2. Honda R&D Americas, Inc., 21001 State Route 739, Raymond, OH, 43067, USA;3. ArcelorMittal Global R&D, 3001 E Columbus Drive, E. Chicago, IN, 46312, USA;1. Medicinal Chemistry, Fibrosis and Lung Injury DPU, Respiratory Therapeutic Area, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom;2. Platform Technology & Science, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom;1. Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan;2. College of Pharmacy, Department of Pharmacology and Toxicology, The University of Arizona, Tucson, AZ 85721, USA;1. Medicinal Chemistry, Fibrosis and Lung Injury DPU, Respiratory Therapeutic Area, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom;2. Platform Technology & Science, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom;3. Global Spectroscopy, Structural and Metabolite ID, Platform Technology and Science, GlaxoSmithKline, 709, Swedeland Road, King of Prussia, PA 19087, United States;4. Platform Technology and Science, GlaxoSmithKline, Five Moore Drive, Research Triangle Park, NC 27709-3398, United States |
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| Abstract: | The unexpected (3S,4R)-3-(R)-1-(hydroxy)ethyl]-4-(2′R,6′S)-1′-oxo-2′-(N-benzyloxy-N-methyl)aminocyclohexen-6′-yl]-1-(t-butyl-dimethylsilyl)azetidin-2-one was one of the main reaction products of the Lewis acid catalysed condensation of (3S,4R)-3-(R)-1-(t-butyl-dimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one with 1-trimethylsilyloxy-6-(N-benzyloxycarbonyl-N-methylamino)cyclohexene. Its absolute configuration was established by NMR experiments on the corresponding, conformationally rigid, acetonide derivative. |
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