| Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid. | |
| | |
MedLine Citation:
|
PMID: 16631765 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
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. |
| | |
Authors:
|
Akio Ichikawa; Hiroshi Ono |
Related Documents
:
|
23598925 - Silver-catalyzed amidation of benzoylformic acids with tertiary amines via selective ca... 12884375 - Determination of absolute configuration using ab initio calculation of optical rotation. 7938265 - Identification and characterization of inhibitors of peptido-leukotriene-synthesis from... 8955075 - Fatty acid ethyl esters, nonoxidative metabolites of ethanol, accelerate the kinetics o... 22806345 - A natural mutation-led truncation in one of the two aluminum-activated malate transport... 10197045 - Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of ... |
Publication Detail:
|
Type: Journal Article Date: 2006-04-24 |
Journal Detail:
|
Title: Journal of chromatography. A Volume: 1117 ISSN: 0021-9673 ISO Abbreviation: J Chromatogr A Publication Date: 2006 Jun |
Date Detail:
|
Created Date: 2006-05-15 Completed Date: 2006-08-14 Revised Date: 2009-01-15 |
Medline Journal Info:
|
Nlm Unique ID: 9318488 Medline TA: J Chromatogr A Country: Netherlands |
Other Details:
|
Languages: eng Pagination: 38-46 Citation Subset: IM |
Affiliation:
|
National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan. ichikawa@affrc.go.jp |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Animals Beetles / chemistry* Heptanol / analogs & derivatives*, chemistry Naphthalenes / chemistry* Pheromones / chemistry* Propionic Acids / chemistry* Spectrum Analysis / methods* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
|
0/2-methoxy-2-(1-naphthyl)propionic acid; 0/2-methyl-4-heptanol; 0/Naphthalenes; 0/Pheromones; 0/Propionic Acids; 111-70-6/Heptanol |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Determination of chloramphenicol residues in meat, seafood, egg, honey, milk, plasma and urine with ...
Next Document: Characterization of concentrated colloidal ceramics suspension: a new approach.