Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1995-10-25
1997-10-14
Lankford, Blaine
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435177, 435195, 435197, 435198, 435123, 435155, 435280, C12P 700, C12N 914, C12N 920
Patent
active
056771550
ABSTRACT:
A process for preparing the sex pheromone of Lymantria dispar L. effectively which comprises the steps of reacting 1-bromodecane and propargyl alcohol tetrahydropyranylether in the presence of sodium hydroxide to give 1-tetrahydropyranyloxy-2-tridecyne, treating the tetrahydropyranyloxy-2-tridecyne with p-toluenesulfonic acid to give 2-tridecyn-1-ol, catalystic-hydrogenating the 2-tridecyn-1-ol in the presence of Lindlar catalyst to give (Z)-2-tridecen-1-ol, oxidizing the (Z)-2-tridecen-1-ol with peroxide to give (.+-.)-cis-2,3-epoxy-1-tridecanol, reacting the (.+-.)-cis-2,3-epoxy-1-tridecanol with acid anhydride in the presence of hydrolase in an organic solvent for a stereoselective acylation and recovering unreacted optically active (2R, 3S)-cis-2,3-epoxy-1-tridecanol after the acylation, reacting the optically active (2R, 3S)-cis-2,3-epoxy-1-tridecanol with toluenesulfonylchloride to give (2R, 3S)-cis-1-p-toluenesulfoxy-2,3-epoxytridecane, and reacting the (2R, 3S)-cis-1-p-toluenesulfoxy-2,3-epoxytridecane with di(4-methylpentyl) lithium copper reagent to yield (7R, 8S)-cis-2-methyl-7,8-epoxyoctadecane which is the sex pheromone of Lymantria dispar L.
REFERENCES:
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4732853 (1988-03-01), Whitesides et al.
patent: 4923810 (1990-05-01), Walts et al.
patent: 4996158 (1991-02-01), Oda et al.
patent: 5213975 (1993-05-01), Fukusaki et al.
patent: 5463149 (1995-10-01), Fukumoto et al.
Vig et al. Indian J. Chem. vol. 24B, 1985 pp. 860-861.
Chan et al. J. Organometallic Chem. vol. 285 pp. 109-119 1985.
Fukusaki Eiichiro
Omata Tetsuo
Senda Shuji
Lankford Blaine
Nitto Denko Co. Ltd.
Tate Christopher R.
LandOfFree
Process for preparing the sex pheromone of Lymantria dispar L does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for preparing the sex pheromone of Lymantria dispar L, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing the sex pheromone of Lymantria dispar L will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1554363