162691-72-7Relevant academic research and scientific papers
Stereoselective synthesis of the sex pheromone of the yellow mealworm using (S)-4-benzyloxazolidinone as chiral auxiliary
Li,Lu,Yang,Chen
, p. 440 - 443 (2010)
(R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworn (Tenebrio molitor L.), was synthesized with high stereoselectivity using (S)-4-benzyloxazolidinone as chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addit
Stereoselective synthesis of sex pheromone (R)-4-Methyl-1-nonanol: Non-cross-linked polystyrene supported oxazolidinone as a chiral auxiliary
Lu, Cuifen,Li, Donglai,Wang, Qiuyan,Yang, Guichun,Chen, Zuxing
experimental part, p. 1078 - 1081 (2009/07/19)
(R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworm (Tenebrio Molitor L.), was synthesized by using non-cross-linked polystyrene supported oxazolidinone as a chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael a
THE RACEMIC FORM AND THE TWO ENANTIOMERS OF 4-METHYL-1-NONANOL, A SEX ATTRACTANT OF THE YELLOW MEALWORM, Tenebrio molitor L.
Carpita, Adriano,Magistris, Elisabetta De,Rossi, Renzo
, p. 99 - 106 (2007/10/02)
The racemic form of 4-methyl-1-nonanol, (R)(S)-1, a sex attractant secreted by the female of the yellow mealworm, has been synthesized in 31 percent overall yield from commercially available methyl 2-octynoate, 2.Almost enantiomerically pure (R)- and (S)-1 have been stereospecifically synthesized in 21.3 and 23.9 percent overall yields, respectively, starting from methyl hydrogen (R)-3-methylglutarate, (R)-3.A precursor for (S)-1, i.e. (S)-3-methyloctanoic acid, (S)-4, has been also prepared in 84 percent yield and over 96 percent enantiomeric purity by the BF3-mediated 1,4-addition of n-pentylcopper to (-)-8-phenylmenthyl crotonate, 15, followed by saponification.The enantiomeric purities of methyl (R)-3-methyloctanoate, (R)-7, and (S)-3-methyl-1-octanol, (S)-8, have been determined by converting these compounds into (R)- and (S)-3-methyloctanoic acid, (R)-4 and (S)-4, respectively, followed by GLC analysis of the corresponding 1-(1-naphthyl)ethylamides obtained from nearly optically pure (R)-1-(1-naphthyl)ethylamine.
