175170-59-9

Upstream product

• 5949-05-3 (S)-Citronellal 
• 138524-36-4 benzyl ether of 3(S),7-dimethyloctane-1,6-(R,S)-7-triol 
• 100-44-7 benzyl chloride 
• 84237-05-8 (S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene 
• 67245-14-1 (3S,6RS)-1-benzyloxy-6,7-epoxy-3,7-dimethyloctane 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 138604-47-4 (S)-6-benzyloxy-4-methylhexanal 

Downstream Products

• 1312554-84-9 C₃₃H₅₀Br₂O₂Si 
• 1312554-85-0 (S)-7-((S)-5-benzyloxy-3-methyl-pentyl)-5,6-bis(bromomethyl)-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalen-2-ol 
• 1312554-88-3 [(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-1-yl]-methanol 
• 1312554-82-7 [(S)-3-((E)-(S)-7-benzyloxy-5-methyl-hept-1-enyl)-2,2-dimethyl-cyclohex-3-enyloxy]-tert-butyl-dimethyl-silane 
• 1312554-83-8 (S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 59614-85-6 (-)-(S)-3-methylheptanoic acid 

Relevant academic research and scientific papers

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

A practical synthesis of 3(S)-methyl-heptanoic acid from (S)-citronellol

Chiral 3-methyl-heptanoic acid is readily accessible by functional group manipulation of optically active citronellol. In principle, this approach is general and could be applied to the synthesis of chiral 3-methyl-alkanoic acids seven carbon atoms in length and longer.