254435-67-1

Upstream product

• 120925-50-0 (R)-2-methyloctan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 254435-66-0 (R)-2-methyl-1-octanol tetrahydropyranyl ether 
• 693-25-4 n-pentylmagnesium bromide 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 737776-63-5 (R)-2-Methoxymethyl-1-(1'-propylidenamino)-pyrrolidine 
• 261926-17-4 (R)-tert-butyl-dimethyl-(2-methyl-octyloxy)-silane 

Downstream Products

• 254435-73-9 (7R,9RS,11S)-7,11-dimethyl-9-phenylsulfonylheptadecane 
• 254435-70-6 (R)-3-methyl-1-(phenylsulfonyl)nonane 
• 570394-40-0 1-methoxy-4-[(2S),(6R)-2,4,6-trimethyl-dodec-3-enyloxymethyl]-benzene 

Relevant academic research and scientific papers

Synthesis of the (5S,9R)-isomer of 5,9-dimethylpentadecane, the major component of the female sex pheromone of the coffee leaf miner moth, Leucoptera coffeella

(5S,9R)-5,9-Dimethylpentadecane, one of the stereoisomers of the major component of the female sex pheromone of the coffee leaf miner moth (Leucoptera coffeella), was synthesized by starting from (R)-3-methyl-4-butanolide and (S)-citronellal.

The synthesis of deoxyfusapyrone. 2. Preparation of the bis-trisubstituted olefin fragment and its attachment to the pyrone moiety

A convergent and modular synthesis has been devised to construct the eight diastereoisomers of deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the

Asymmetric synthesis of all stereoisomers of 7,11-dimethylheptadecane and 7-methylheptadecane, the female pheromone components of the spring hemlock looper and the pitch pine looper

The asymmetric synthesis of the stereoisomers of 7,11-dimethylheptadecane (1) and 7-methylheptadecane (2) via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction and good overall yields is described. A mixture of (7S,11R)-1 and (S)-2 is the female-produced sex pheromone of the spring hemlock looper moth (Lambdina athasaria) and the pitch pine looper moth (Lambdina pellucidaria). They are both forest pests in northeastern North America.

Pheromone synthesis, CXCIX([≠]). Synthesis of all the stereoisomers of 7-methylheptadecane and 7,11-dimethylheptadecane, the female sex pheromone components of the spring hemlock looper and the pitch pine looper

All the stereoisomers of 7-methylheptadecane (1) and 7,11- dimethylheptadecane (2) were synthesized by starting from the enantiomers of citronellol (3) and methyl 3-hydroxy-2-methylpropanonate (8), respectively. A short synthesis of meso-7,11-dimethylheptadecane [(7R, 11S)-2] was achieved starting from meso-2,6-dimethylheptanedioic acid [(2R,6S)21]. A mixture of (S)-1 and (7R, 11S)-2 is the pheromone of the spring hemlock looper moth (Lambdina athasaria) and the pitch pine looper moth (L. pellucidaria).

Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity

The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol 8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatograghic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.