249745-83-3

Upstream product

• 159213-03-3 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide 
• 177088-48-1 (2R)-2-methyl-1-iodohexane 
• 66050-98-4 (2R)-methyl-1-hexanol 
• 159345-07-0 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylhexanamide 
• 90-82-4 pseudoephedrine 

Relevant academic research and scientific papers

Sex pheromone of the pine sawfly, Macrodiprion nemoralis. Stereoselective synthesis of the sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate

The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-γ-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.