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J Chromatogr A

Title:		"Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid"
Author(s):		Ichikawa A; Ono H;
Address:		"National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan. ichikawa@affrc.go.jp"
Journal Title:		J Chromatogr A
Year:		2006
Volume:		20060424
Issue:		1
Page Number:		38 - 46
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"