149065-61-2Relevant academic research and scientific papers
Chemical development of an α2δ ligand, (3 S,5 R)-3-(Aminomethyl)-5-methyloctanoic acid
Murtagh, Lorraine,Dunne, Catherine,Gabellone, Gino,Panesar, Niamh J.,Field, Stuart,Reeder, Lisa M.,Saenz, James,Smith, George P.,Kissick, Kyle,Martinez, Carlos,Van Alsten, John G.,Evans, Margaret C.,Franklin, Lloyd C.,Nanninga, Thomas,Wong, John
, p. 1315 - 1327 (2012/01/12)
Three synthetic approaches, suitable for the large scale manufacture of the α2δ-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocentre was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.
Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
, p. 111 - 121 (2007/10/03)
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.
