66007-17-8

Upstream product

• 51018-58-7 (S,Z)-(+)-14-methyl-8-hexadecen-1-ol 
• 37610-80-3 1,3-dioxolan-2-ylethylmagnesium bromide 
• 114905-16-7 Acetic acid (Z)-9-[1,3]dioxolan-2-yl-non-2-enyl ester 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 534-00-9 (S)-2-methylbutyl bromide 
• 59177-09-2 (S)-1-bromo-6-methyloctane 
• 1730-91-2 (S)-2-Methylbutyric acid 
• 5856-79-1 iso-butyl chloroformate 
• 114862-08-7 ((S)-6-methyloctyl)triphenylphosphonium bromide 
• 110453-78-6 (S)-(+)-6-methyl-1-octanol 
• 114925-59-6 (S)-(6-Methyloctyl)tetrahydropyranylether 
• 114862-03-2 N-<(R)-2-Hydroxy-1-phenylethyl>-(R)-2-methylbutyramid 
• 114925-60-9 (S)-14-Methyl-<(Z)-8-hexadecenyl>tetrahydropyranylether 
• 53353-01-8 (S)-1-bromo-4-methylhexane 

Relevant academic research and scientific papers

A practical total synthesis of both e - And Z -isomers of optically pure (S)-14-methylhexadec-8-enal (Trogodermal)

The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey-Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers. Georg

Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group

(R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give a mixture of abnormal products with both longer or shorter carbon chains than the desired product. The specific rotations of 18 newly and 6 previously synthesized compounds with a terminal sec-butyl group were measured to conclude them to be [α]D +3.5 to +6.5 or -3.6 to -6.4.

GLYCALS IN STEREOCHEMICAL SYNTHESIS SYNTHESIS OF (14R,8Z)-TROGODERMAL AND ITS (14S,8Z)-ENANTIOMER FROM DI-O-BENZOYL-D- AND -L-ARABINALS

Enantiomerically pure (14R)-14-methylhexadeca-8Z-enal (cis-trogodermal) - the aggregation pheromone of the khapra beetle (Trogoderma) - and its (14S,8Z)-enantiomer has been effected from di-O-benzoyl-D- and -L-arabinals.

A facile synthesis of (S)-trogodermal

A simple route for the synthesis of (S)-(Z)- and (S)-(E)-14-methyloctadec-8-en-1-al (Ia and Ib) has been developed.The achiral acetylene (9) is alkylated with the chiron bromide (S)-5 in the presence of BuLi as the base to give 10.This on subsequent functionalisation furnishes both Ia and Ib.

Pheromones, 67. - Synthesis of the Enantiomers of (Z)-14-Methyl-8-hexadecenal , the Pheromone of Some Trogoderma Species (Coleoptera: Dermestidae)

The separation of diastereomeric phenylglycinolamides of 2-methylbutyric acid by means of MPLC yields the pure enantiomers of the acid, from which (R,Z)- and (S,Z)-14-methyl-8-hexadecenal (1) (trogodermal) can be obtained.