85514-80-3

Upstream product

• 936650-20-3 (11R,12R,13R,14R)-11,14-bis(benzyloxy)tetracosane-12,13-diol 
• 100-39-0 benzyl bromide 
• 936650-19-0 (4S,5S)-4,5-bis((R)-1-hydroxyundec-1-yl)-2,2-dimethyl-1,3-dioxolane 
• 936650-18-9 (4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane 
• 85514-79-0 (2S,3S,4R)-4-Benzyloxy-tetradecane-2,3-diol 

Downstream Products

• 105581-92-8 (4R,5R)-1-phenyl-5-(benzyloxy)-4-pentadecanol 
• 105581-99-5 (6R,7R)-7-(benzyloxy)-heptadec-1-en-6-ol 
• 105582-00-1 (6S,7R)-7-(benzyloxy)-heptadec-1-en-6-ol 
• 85514-82-5 (R)-2-(benzyloxy)-1-dodecanol 
• 936650-21-4 (4R,5R)-5-(benzyloxy)pentadec-1-en-4-ol 
• 936650-22-5 (4R,5R)-5-(benzyloxy)-4-(p-toluenesulfonyloxy)pentadec-1-ene 
• 936650-23-6 (7R,8R)-8-(benzyloxy)-7-(p-toluenesulfonyloxy)-2-methyloctadec-4-ene 
• 936650-24-7 (4R,5R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)pentadec-1-ene 
• 936650-26-9 (11R,12R)-12-(tert-butyldimethylsilyloxy)-17-methyloctadecan-11-yl-4-methylbenzenesulfonate 
• 54910-51-9 (2S-cis)-7,8-epoxy-2-methyloctadecane 
• 105243-14-9 (7R,8R)-(+)-8-hydroxy-7-p-toluenesulfonyloxy-2-methyloctadecane 
• 105582-05-6 (5R,6R)-5-acetoxy-6-(benzyloxy)hexadecanoic acid 
• 105582-06-7 (5S,6R)-5-acetoxy-6-(benzyloxy)hexadecanoic acid 
• 105582-03-4 (5R,6R)-5-acetoxy-6-(benzyloxy)hexadecanal 

Relevant academic research and scientific papers

Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlure

(Chemical Equation Presented) Enantiodivergent synthesis of both (-)- and (+)-disparlure, a bioactive pheromone, possessing a cis-epoxide has been accomplished. The key step involves the cross metathesis of a chiral homoallylic alcohol derived from L-(+)-tartaric acid.

Asymmetric Synthesis of (5R,6S)-6-Acetoxy-5-hexadecanolide, the Major Component of the Oviposition Attractant Pheromone of the Mosquito Culex pipens fatigans, and Two of Its Stereoisomers

The benzyl derivatives of (R)- and (S)-2-hydroxydodecanal have been prepared by a previously described asymmetric synthesis based on a chiral 1,3-oxathiane and have been converted into (5R,6S)-6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone, and its 5R,6R and 5S,6R stereoisomers in highly diastereoselective fashion.The steps involved are Grignard addition of 5-pentenylmagnesium bromide, Mitsunobu inversion for one of the erythro (5R,6S) isomers and oxidation-hydride reduction for the other, ozonization, oxidation, lactone formation, debenzylation, and acetylation, the overall yield in these steps being 30-42percent.