459166-35-9

Upstream product

• 917-54-4 methyllithium 
• 38261-81-3 (S)-2-methylbutyl tosylate 
• 112-43-6 10-Undecen-1-ol 
• 100-39-0 benzyl bromide 
• 81518-75-4 ((undec-10-en-1-yloxy)methyl)benzene 
• 459166-33-7 (S)-2-(9-(benzyloxy)nonyl)oxirane 
• 459166-34-8 (R)-12-benzyloxy-dodecan-3-ol 
• 358374-73-9 (S)-11-benzyloxy-undecane-1,2-diol 

Downstream Products

• 71777-33-8 (S)-10-methyl-1-dodecanol 
• 71777-35-0 (+)-(S)-10-methyldodecyl acetate 

Relevant academic research and scientific papers

Chiral discrimination of branched-chain fatty acids by reversed-phase HPLC after labeling with a chiral fluorescent conversion reagent

Anteiso fatty acids having 16 to 29 carbon atoms were labeled with the chiral fluorescent conversion reagents, (1R,2R)- and (1S,2S)-2-(2,3- anthracenedicarboximido)-cyclohexanol. The diastereomeric esters of anteiso acids having up to 20 carbon atoms were

Hydrolytic kinetic resolution of terminal mono- and bis-epoxides in the synthesis of insect pheromones

Hydrolytic kinetic resolution (HKR) of functionalised epoxides using (salen)Co(OAc) complexes provides enantiomerically enriched epoxides and diols, which have been transformed into important insect sex pheromones. In this general approach, (-)-(R)- and (+)-(S)-10-methyldodecyl acetates from the smaller tea tortrix moth were obtained, as was (-)-(R)-10-methyltridecan-2-one from the southern corn rootworm. The (S)-epoxide obtained from undec-1-en-6-yne was transformed to (-)-(R)-(Z)-undec-6-en-2-ol (Nostrenol) from ant-lions. HKR of appropriate bisepoxides was also investigated, and transformations of the resulting bisepoxides and epoxydiols provided (-)-(1R,7R)-1,7-dimethylnonylpropanoate from corn rootworms, (-)-(6R,12R)-6,12-dimethylpentadecan-2-one from the female banded cucumber beetle, and (-)-(2S,11S)-2,11-diacetoxytridecane and (+)-(2S,12S)-2,12-diacetoxytridecane from female pea-midges.

Hydrolytic kinetic resolution of mono- and bisepoxides as a key step in the synthesis of insect pheromones

The synthetic utility of the readily separated epoxides, diols, epoxydiols and tetrols of high enantiomeric excesses, obtained by hydrolytic kinetic resolution (HKR) of functionalised mono- and bisepoxides with (salen)Co(OAc) complexes, is demonstrated by their efficient transformations to important insect pheromones.