99427-19-7

Upstream product

• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 97424-48-1 (R)-1-bromo-2-methylhexane 
• 2385-77-5 (R)-Citronellal 
• 83541-12-2 (R)-(+)-citronellyl benzyl ether 
• 237431-14-0 (R)-3-methyl-6-hepten-1-ol 
• 1117-61-9 (3R)-citronellol 
• 146512-86-9 (R)-6-benzyloxy-4-methylhexyl tosylate 
• 146512-85-8 (3R)-1-benzyloxy-3-methyl-6-hexanol 
• 83541-13-3 (R)-(+)-6-(benzyloxy)-4-methylhexanal 
• 99427-16-4 (R)-3-Methyl-6-(tosyloxy)hexyl acetate 
• 20425-54-1 (R)-1-citronellyl acetate 
• 99824-63-2 (R)-2-methylhexyl 4-methylbenzenesulfonate 
• 177314-38-4 (R)-2-Methylhexyl tetrahydropyranyl ether 

Relevant academic research and scientific papers

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica

Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.

Pheromone Syntheses, LXXVII. - New Synthesis of the Enantiomers of 14-Methyl-1-octadecene, the Pheromone of Lyonetia clerkella L.

The synthesis of the title compounds (R)-1 and (S)-1 from (R)-citronellic acid (R)-2 is described.