129100-10-3

Upstream product

• 7729-39-7 10-Methylen-octadecansaeuremethylester 
• 542-47-2 10-Methyl-octadecanoic acid 
• 74-88-4 methyl iodide 
• 917-64-6 methyl magnesium iodide 
• 67-56-1 methanol 
• 16695-31-1 1-(2-Tetrahydropyranyloxy)-7-octyne 
• 4286-55-9 1-bromo-6-hexanol 
• 124-13-0 Octanal 
• 2490-04-2 (R,S)-10-methyloctadecanol 
• 693-54-9 Decan-2-one 
• 186581-53-3 diazomethane 
• 133398-13-7 (R)-10-methyloctadecanoic acid 
• 927888-76-4 (S)-10-methyloctadecanoic acid 
• 158576-26-2 (R,S)-1-iodo-2-methyldecane 

Relevant academic research and scientific papers

A new short synthesis of 10R-tuberculostearic acid and its enantiomer

Tuberculostearic acid (10R-methyloctadecanoic acid) and its 10S-enantiomer were synthesised by a chiral pool strategy, in four steps from citronellyl bromide.

Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates

Tuberculostearic acid (R)-10-methyloctadecanoic acid, is a characteristic component of pathogenic mycobacteria and related organisms.Sensitive detection of this acid infected material allows rapid detection of mycobacterial disease.A novel, convergent synthesis of tuberculostearic acid and key chiral intermediates is described in this communication, to provide a reference compound.Racemic and (R)- and (S)-1-iodo-2-methyldecanes were synthesised from 1-octanal and 1-carboethoxyethylidenetriphenylphosphorane as initial starting materials. 1-Hydroxyoct-7-yne was made from 1,6-hexanediol by two alternative methods and coupled with the above racemic iodide.Hydrogenation and oxidation of the resulting (R,S)-10-methyloctadec-7-yn-1-ol gave racemic tuberculostearic acid. Keywords: Mycobacterium tuberculosis; Tuberculostearic acid; Acetylene coupling; (R,S)-10-methyloctadecanoic acid; Chiral 2-methyl branched fatty acids