77732-39-9

Upstream product

• 39027-57-1 3-(4-methylphenyl)butanoic acid 
• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 1201-85-0 (S)-3-(4-methylphenyl)butanoic acid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 77732-36-6 (S)-3-p-Tolyl-butyryl chloride 

Downstream Products

• 106035-79-4 (R)-3-(4-methylphenyl)-1-butanol 
• 144271-33-0 (3R,1'R)-N-methyl-N-(1-naphthylethyl)-3-(4-methylphenyl)butanamide 

Relevant academic research and scientific papers

Farnesyl-diphosphate synthase. Interplay between substrate topology, stereochemistry, and regiochemistry in electrophilic alkylations

The absolute stereochemistries of 8-OPP, 9-OPP, and 10-OPP obtained from incubation of bisubstrate analogs 1-OPP and 2-OPP with farnesyl-diphosphate synthase were determined by correlation of ORD spectra with those of synthetic materials. Only one enantiomer was found for each of the enzymatic products. The products from 1-OPP were (S)-8-OPP and (S)-10-OPP, while those from 2-OPP were (R)-8-OPP, (R)-9-OPP, and (R)-10-OPP. Conformational analysis of 1-OPP and 2-OPP, which considers topological limitations imposed by FPP synthase, indicates that the products from the enzymatic reactions are formed from discrete E·S complexes formed from different conformers of the substrates. Overlays of the conformations that give the observed products are consistent with a model where the hydrocarbon moieties occupy a central volume flanked on top and bottom by their diphosphate residues.

A novel synthetic method for optically active terpenes by the ring-opening reaction of (R)-(+)-β-methyl-β-propiolactone

Optically active terpene such as (R)-(+)-citronellol, (R)-(+)-pulegone or (S)-ar-turmerone is prepared in high enantiomeric excess from an intermediate, (R)-(+)-citronellic acid or (S)-(+)-3-p-tolylbutyric acid, which is easily prepared by the Sn2 type of ring opening reaction of (R)-(+)-β-methyl-β-propiolactone with homoprenylmagnesium bromide in the presence of a copper(I) salt or di-p-tolylcuprate.