122744-58-5

Upstream product

• 78655-79-5 2(R),3(R) methyl 3-hydroxy-2-methylpentanoate 
• 122744-56-3 1-ethylpropyl 3R-tert-butyldimethylsilyloxy-2R-methylpentanoate 
• 122744-55-2 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoyl chloride 
• 122798-51-0 methyl (2R,3R)-3-t-butyldimethylsilyloxy-2-methylpentanoate 
• 122744-54-1 (2R,3R)-3-t-butyldimethylsilyloxy-2-methylpentanoic acid 
• 42558-50-9 methyl (3R)-3-hydroxypentanoate 
• 584-02-1 2-pentanol 
• 207788-62-3 (R)-3-Hydroxy-pentanoic acid 1-ethyl-propyl ester 
• 122776-43-6 3-Oxo-pentanoic acid 1-ethyl-propyl ester 
• 99-34-3 3,5-dinitrobenzoic acid 
• 122798-52-1 1-ethylpropyl (2R,3R)-3-hydroxy-2-methylpentanoate 

Relevant academic research and scientific papers

A flexible stereocontrolled synthesis of β-hydroxy-α-methyl esters: Application to the synthesis of stegobiol and serricorole

β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is file catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP- Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

Pheromone Synthesis, CXVII. - Synthesis of Sitophilate, the Aggregation Pheromone of Sitophilus granarius L., and Its Antipode

The synthesis of sitophilate was achieved starting from (S)-2.Mitsunobu inversion of 7 to give crystalline 3,5-dinitrobenzoate 8 was the key step to diastereomerically pure 1.The antipode of the pheromone was also synthesized.