71777-35-0

Upstream product

• 71777-33-8 (S)-10-methyl-1-dodecanol 
• 108-24-7 acetic anhydride 
• 143229-16-7 (9-benzyloxy-nonyl)-oxirane 
• 459166-33-7 (S)-2-(9-(benzyloxy)nonyl)oxirane 
• 459166-35-9 (S)-1-benzyloxy-10-methyldodecane 
• 459166-34-8 (R)-12-benzyloxy-dodecan-3-ol 
• 358374-73-9 (S)-11-benzyloxy-undecane-1,2-diol 
• 54156-71-7 (S)-2-methylbut-1-yltriphenylphosphonium bromide 
• 127914-31-2 (Z)-(10-Methyl-8-dodecenyl)-tetrahydropyranylether 
• 127914-32-3 (10-Methyldodecyl)tetrahydropyranylether 
• 534-00-9 (S)-2-methylbutyl bromide 
• 57221-80-4 8-tetrahydropyranyloxyoctanal 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 81518-75-4 ((undec-10-en-1-yloxy)methyl)benzene 

Relevant academic research and scientific papers

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.

Pheromones, 76. Synthesis of the Enantiomers of 10-Methyldodecyl Acetate and 12-Methyltetradecyl Acetate, Chiral Pheromone Components of Adoxophyes Species (Lepidoptera: Tortricidae)

From enantiomeric (R)-(-)- and (S)-(+)-2-methylbutyl bromide (3), available by resolution of (R)-(-)-phenylglycinol amides of rac-2-methylbutanoic acid, and from enantiomeric 6-methyloctyl bromide (7) the corresponding phosphonium salts were obtained.Wittig olefination yielded the optically active methyl-branched olefinic THP ethers 12 and 13, hydrolysis, catalytic hydrogenation, and acetylation gave rise to the formation of the chiral title compounds (R)-(-)- and (S)-(+)-10-methyldodecyl acetate (1) and (R)-(-)- and (S)-(+)-12-methyltetradecyl acetate (2).

Synthesis of the chiral components of the sex pheromone of Adoxophyes leaf roller moths

The optically pure (R) and (S) enantiomers of 10-methyldodecyl acetate were synthesized from (R)-5-acetoxy-4-methylpentanoic acid and (S)-2-methylbutanol, respectively, using the condensation of (R)- and (S)-2-methylbutylmagnesium bromides with 8-tosyloxyoctyl acetate in the presence of Li2CuCl4 in the key step.