459166-34-8

Upstream product

• 459166-33-7 (S)-2-(9-(benzyloxy)nonyl)oxirane 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 358374-73-9 (S)-11-benzyloxy-undecane-1,2-diol 
• 100-39-0 benzyl bromide 
• 112-43-6 10-Undecen-1-ol 
• 143229-16-7 (9-benzyloxy-nonyl)-oxirane 
• 81518-75-4 ((undec-10-en-1-yloxy)methyl)benzene 

Downstream Products

• 71777-33-8 (S)-10-methyl-1-dodecanol 
• 71777-35-0 (+)-(S)-10-methyldodecyl acetate 
• 459166-35-9 (S)-1-benzyloxy-10-methyldodecane 
• 612070-03-8 (R)-10-(t-butyldiphenylsilanyloxy)dodecan-1-ol 
• 612070-04-9 (R)-10-(t-butyldiphenylsilanyloxy)dodecanal 

Relevant academic research and scientific papers

Products of cytochrome P450Biol (CYP107H1)-catalyzed oxidation of fatty acids

(Matrix presented) Oxidation of tetradecanoic and hexadecanoic acids by cytochrome P450Biol (CYP107H1) produces mainly the 11-, 12-, and 13-hydroxy C14 fatty acids and the 11- to 15-hydroxy C16 fatty acids, respectively. In contrast to previous reports, terminal hydroxylation is not observed. The enantiospecificity of fatty acid hydroxylation by P450Biol was also determined, and the enzyme was shown to be moderately selective for production of the (R)-alcohols.

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.