Synthesis and analytical properties of (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid |
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| Institution: | 1. National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan;2. National Food Research Institute, 2-1-12 Kannondai, Tsukuba, Ibaraki 305-8642, Japan;3. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba, Sendai 980-8577, Japan;1. Department of Chemistry, Goucher College, Baltimore, MD 21204, United States;2. University of New Mexico Cancer Center, Albuquerque, NM 87131, United States;1. Eskitis Institute, Griffith University, Brisbane, QLD 4111, Australia;2. Queensland Museum, South Brisbane, QLD 4101, Australia;2. Institution of Entomology, College of Life Science, Nankai University, Tianjin 300071, China;1. Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700 032, India;2. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah 711 103, India;3. Department of Chemistry, National Institute of Technology Agartala, Tripura (W) 799 046, India;1. Department of Chemistry, College of Natural Sciences, Chungnam National University, Daejeon 305-764, Republic of Korea;2. Yonsung Fine Chemicals R&D Center, Suwon 443-380, Republic of Korea |
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| Abstract: | 2-Methoxy-2-(9-phenanthryl)propionic acid was synthesized as a novel chiral resolving agent. The absolute configuration of (+)-2-methoxy-2-(9-phenanthryl)propionic acid was determined to be S by using X-ray structural analysis of the (1R,2S,5R)-menthyl ester. In the crystal, the methoxyl and carbonyl groups of the ester are in a syn-periplanar position. The syn-periplanar conformations of (1R,2S,5R)-menthyl esters were also observed by the NMR analyses in CDCl3. The utility of (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid was exemplified by the resolution of (±)-3-octanol. |
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