99833-15-5

Upstream product

• 131906-75-7 (S)-2-Methylhexyl Tetrahydropyranyl Ether 
• 98-59-9 p-toluenesulfonyl chloride 
• 177607-70-4 (S)-4-benzyl-3-((S)-2-methylhexanoyl)oxazolidin-2-one 
• 143965-32-6 (4S)-3-hexanoyl-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 142-61-0 Hexanoyl chloride 
• 624-22-6 (2S)-2-methyl-1-hexanol 

Downstream Products

• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 131906-84-8 (5S,7RS,9S)-5,9-Dimethyl-7-(phenylsulfonyl)heptadecane 
• 131906-85-9 (5S,7RS,9S)-5,9-Dimethyl-7-phenylsulfonyloctadecane 
• 108195-53-5 (5S,9S)-5,9-Dimethylheptadecane 
• 251968-34-0 (3S)-methyl-1-tosyloxyheptane 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 97424-48-1 (S)-1-bromo-2-methylhexane 

Relevant academic research and scientific papers

A facile asymmetric synthesis of (S)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li 2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.

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 synthesis, CXCII. - Synthesis of all the stereoisomers of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane and 5,9- dimethylheptadecane, the sex pheromone components of the apple leafminer, Lyonetia prunifoliella

All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9- dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of ci

Pheromone Synthesis, CXXIX - Synthesis of the (5S,9S)-Isomers of 5,9-Dimethylheptadecane and 5,9-Dimethyloctadecane, the Major and the Minor Components of the Sex Pheromone of Leucoptera malifoliella Costa

The synthesis of (5S,9S)-5,9-dimethylheptadecane (1) as well as that of (5S,9S)-5,9-dimethyloctadecane (2) has been achieved by starting from methyl (R)-3-hydroxy-2-methylpropanoate (3a) and (S)-citronellal (7). --- Key Words: Heptadecane, 5,9-dimethyl- /