443361-62-4

Upstream product

• 859436-76-3 (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 
• 1609197-51-4 (2S,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 
• 443361-58-8 (R)-3,7-Dimethyl-oct-6-ene-1,2,3-triol 
• 443361-64-6 (3R)-(-)-3,7-dimethyl-1,2-epoxy-6-octen-3-ol 
• 126-91-0 linalool 
• 158060-34-5 (2R,3R)-3,7-dimethyl-6-octene-1,2,3-triol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 62777-72-4 (2R,3S)-2,3-epoxynerol 
• 125874-95-5 (2S,3R)-3,7-dimethyl-2,3-epoxy-6-octenyl acetate 
• 859436-75-2 (2R,3S)-3,7-dimethyl-2,3-epoxy-6-octenyl acetate 
• 443361-60-2 1-(tert-butyl-diphenyl-silanyloxy)-3,7-dimethyl-oct-6-ene-2,3-diol 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer

An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate.

Enzyme-assisted synthesis of (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle, and its (R)-enantiomer

(S)-1,3-Dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle (Leptinotarsa decemlineata), and its (R)-isomer were synthesized by employing lipase-catalyzed asymmetric acetylation of (±)-2,3-epoxynerol as the key step.

(S)-3,7-Dimethyl-2-oxo-6-octene-1,3-diol: An aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata (Say)

(S)-3,7-Dimethyl-2-oxo-6-octene-1,3-diol has been identified as a male-produced pheromone from the Colorado potato beetle. Its gross structure was deduced from its mass and NMR spectra plus synthesis from geraniol. The absolute configuration was determined to be (S) by syntheses of both enantiomers from (R)- and (S)-linalool, respectively.