99439-79-9

Usage

Uses

Used in Chemical Synthesis:
Heptanoic acid, 3-methyl-, methyl ester, (S)is used as a reagent in the synthesis of stereoisomers of 5,9-dimethylheptadecane, which is the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella). This application is important for studying the mating behavior and chemical communication of these moths, as well as for developing pest control strategies that target their reproductive processes.

Upstream product

• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 
• 107-92-6 butyric acid 
• 693-03-8 n-butyl magnesium bromide 
• 623-43-8 crotonic acid methyl ester 
• 22104-69-4 (E)-methyl 2-heptenoate 
• 75-16-1 methylmagnesium bromide 
• 26549-24-6 (2R)-hexan-2-ol 
• 1393538-40-3 (S)-2-(1-methylpentyl)malonic acid dimethyl ester 
• 1393538-39-0 (R)-2-hexanyl tosylate 

Downstream Products

• 59614-85-6 (-)-(S)-3-methylheptanoic acid 
• 27608-03-3 (R)-3-methylheptanal 
• 1393538-53-8 (5S,9R)-5,9-dimethyl-8-(4-methylphenylsulfonyl)heptadecane 
• 1393538-58-3 (5S,9S)-5,9-dimethyl-8-(4-methylphenylsulfonyl)heptadecane 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 108195-53-5 (5S,9S)-5,9-Dimethylheptadecane 

Relevant academic research and scientific papers

Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis.

A general strategy for the introduction of stereogenic centers bearing a methyl group: Total synthesis of sex pheromones

We're bringing sexy back: The highly efficient introduction of stereogenic centers bearing methyl group by conjugate addition of RMgBr to α,β-unsaturated esters has been employed in the total syntheses of two sex pheromones (see scheme). Binap=[1,1'-binaphthalene]-2,2'- diylbis(diphenylphosphane). Copyright

Highly efficient copper(I) iodide-tolyl-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to α,β-unsaturated esters

A highly efficient asymmetric conjugate addition of methylmagnesium bromide (MeMgBr) to α,β-unsaturated esters catalyzed by copper(I) iodide-tolyl-BNIP (CuI-Tol-BINAP) is described.

Copper-catalyzed enantioselective conjugate addition of Grignard reagents to α,β-unsaturated esters

(Chemical Equation Presented) Stable dinuclear Cu complexes have been used to catalyze the conjugate addition of inexpensive and readily available Grignard reagents to acyclic α,β-unsaturated esters. The method provides the correspending β-substituted optically active esters in high yields and with excellent enantioselectivities (see scheme). R3 = cyclohexyl, R 4 = Ph or R3 = Ph, R4 = cyclohexyl.

Asymmetric Conjugate Addition of Organometallic Reagents to Chiral Vinyl Sulfoximines

The chiral vinyl sulfoximines 1 and 2 (R' = C6H5, CH3, n-Bu, C6H5CH2CH2) have been prepared; they undergo conjugate addition reactions with organometallic reagents with high asymmetric induction.These conjugate addition adducts have been converted to chiral 3-alkylalkanoic acids in high enantiomeric excess (>90percent)