85880-35-9

Upstream product

• 22644-30-0 (R)-2-methylbut-3-en-1-ol 
• 10422-35-2 1-bromo-2-methyl-butane 
• 143-33-9 sodium cyanide 
• 87106-24-9 (S)-3-methyl-1,5-pentanediol monotosylate monobenzyl ether 
• 105485-71-0 ethyl 2-carbethoxy-4,8-dimethyldecanoate 
• 105485-68-5 ethyl 4,8-dimethyldecanoate 
• 105485-65-2 rhodinal 
• 245118-38-1 (2R/S,6S)-(+)-2,6-dimethyl-1-octanol 
• 105500-65-0 1-bromo-2,6-dimethyloctane 
• 105485-66-3 2,6-dimethyl-1-octene 
• 28339-05-1 4,8-dimethyldecan-1-ol 
• 99032-67-4 (S)-(+)-1-bromo-2-methylbutane 
• 110659-29-5 (R)-2-methyl-3-buten-2-yl tosylate 
• 114905-27-0 (6S,3RS)-2,3-isopropylidenedioxy-2,6-dimethyl-7-octene 

Downstream Products

• 87106-39-6 4(RS),8(S)-dimethyldecanal dimethyl acetal 

Relevant academic research and scientific papers

Synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal: the common aggregation pheromone of flour beetles

The synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal 1 and 1a has been achieved connecting the chiral building block (R)-2-methyl-1-bromobutane 4 with (R)- and (S)-citronellol derivatives. The key intermediate 4 was obtained optically pure in five steps from methyl (S)-3-hydroxy-2-methylpropionate 2.

A NEW SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL - THE PHEROMONE OF THE MEAL WORMS Tribolium confusum AND Tribolium castaneum

A method of synthesis was developed for (4R,8R)-4,8-dimethyldecanal - the aggregation pheromone of the meal worms Tribolium confusum and T. castaneum.It contains altogether 12 stages and uses (R)-(+)-5-acetoxy-4-ethylpentanoic acid and (S)-(+)-3,7-dimethyl-1,6-octadiene as the initial chiral compounds.The overall yield of the pheromone amounted to 27percent on the initial acid or 15percent on the initial diene.The optical purity of the chiral centers C-4 and C-8 in the molecule of the pheromone was estimated as ca. 55 and ca. 97percent respectively.

Synthesis of 4(RS),8(S)-Dimethyldecanal: An Aggrigation Pheromone of Red Flour Beetles

A simple and straight forward synthesis of the pheromone 4(RS),8(S)-dimethyldecanal (IX) has been described starting from 7-hydroxycitronellal (I).

SYNTHESIS OF ALL OF THE FOUR POSSIBLE STEREOISOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF THE FLOUR BEETLES

The four stereoisomers of 4,8-dimethyldecanal were synthesized employing organometallic or electrolytic coupling reactions as the key step.The response of the red flour beetle, Tribolium castaneum, to the (4R,8R)-isomer was identical with that to the natural pheromone, while other isomers induced only very weak or no responses.The (4R,8R)-isomer is therefore the natural pheromone.