Title: | "Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid" |
Address: | "National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan. ichikawa@affrc.go.jp" |
DOI: | 10.1016/j.chroma.2006.03.100 |
ISSN/ISBN: | 0021-9673 (Print) 0021-9673 (Linking) |
Abstract: | "To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using (S)-MalphaNP acid. As a chiral-resolving agent, MalphaNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MalphaNP esters was observed when n-hexane-THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MalphaNP esters gave (R)-2-methyl-4-heptanol and its enantiomer; enantiopure (S)-MalphaNP acid was also recovered. In addition, the preferred conformation of the MalphaNP ester was confirmed using methyl (R)-3-hydroxyvalerate as an authentic compound" |
Keywords: | Animals Coleoptera/*chemistry Heptanol/*analogs & derivatives/chemistry Naphthalenes/*chemistry Pheromones/*chemistry Propionates/*chemistry Spectrum Analysis/*methods Stereoisomerism Sulfhydryl Compounds; |
Notes: | "MedlineIchikawa, Akio Ono, Hiroshi eng Netherlands 2006/04/25 J Chromatogr A. 2006 Jun 2; 1117(1):38-46. doi: 10.1016/j.chroma.2006.03.100. Epub 2006 Apr 24" |