96924-72-0

Upstream product

• 27151-65-1 3-methyl-1,5-pentanedioic acid monomethyl ester 
• 32365-96-1 methyl 3-(R)-methyl-5-hydroxypentanoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 

Downstream Products

• 21964-49-8 tetradeca-1,13-diene 
• 96924-75-3 methyl (R)-3-methyl-11-dodecenoate 
• 86423-92-9 (3R)-3-Methylhexan-1-ol 
• 866751-08-8 Toluene-4-sulfonic acid (R)-5-(4'-chloro-biphenyl-4-yloxy)-3-methyl-pentyl ester 
• 866751-11-3 Toluene-4-sulfonic acid (R)-3-methyl-5-(2-oxo-3-pyridin-4-yl-imidazolidin-1-yl)-pentyl ester 
• 866751-04-4 (R)-5-(4'-Chloro-biphenyl-4-yloxy)-3-methyl-pentanoic acid methyl ester 
• 162691-72-7 (R)-3-methyloctyl-4-methylbenzenesulfonate 
• 118665-25-1 (S)-4-methyl-1-nonanol 

Relevant academic research and scientific papers

Synthesis and antipicornavirus activity of (R)- and (S)-1-[5-(4′- chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one

The new pyridyl imidazolidinone derivative, 1-[5-(4′-chlorobiphenyl- 4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one (±)-1a, was synthesized and found to have an excellent antiviral activity against EV71 (IC50 = 0.009 μM). Therefore, both the enantiomers, (S)-(+)-1a and (R)-(-)-1a, have been prepared starting from readily available monomethyl (R)-3-methylglutarate (7) as a useful chiral building block and their antiviral activity was evaluated in a plaque reduction assay. Interestingly, we observed that the enantiomer (S)-(+)-1a was 10-fold more active against enterovirus71 (EV71) (IC50 = 0.003 μM) than the corresponding enantiomer (R)-(-)-1a (IC50 = 0.033 μM). Similar results were found against all five strains (1743, 2086, 2231, 4643, and BrCr) of EV71 tested. This demonstrated that the absolute configuration of the chiral carbon atom at the 3-position of the alkyl linker considerably influenced the anti-EV71 activity of these pyridyl imidazolidinones.

Imidazolidinone compounds

This invention relates to compounds of the following formula: in which R1, R2, A1, A2, X, Y, m, n, p, x and y are as defined herein, pharmaceutical compositions comprising the compounds and use of the compounds in treating enterovirus infection.

Analysis of the labial gland secretion of the cuckoo-bumblebee (Psithyrus vestalis) males and synthesis of abundant geranylcitronellol

Labial glands of the cuckoo-bumblebee males of the species Psithyrus vestalis were extracted and the components of their secretions were identified. Chemical composition of the males' signal of Psithyrus vestalis has not yet been described in the literatu

THE RACEMIC FORM AND THE TWO ENANTIOMERS OF 4-METHYL-1-NONANOL, A SEX ATTRACTANT OF THE YELLOW MEALWORM, Tenebrio molitor L.

The racemic form of 4-methyl-1-nonanol, (R)(S)-1, a sex attractant secreted by the female of the yellow mealworm, has been synthesized in 31 percent overall yield from commercially available methyl 2-octynoate, 2.Almost enantiomerically pure (R)- and (S)-1 have been stereospecifically synthesized in 21.3 and 23.9 percent overall yields, respectively, starting from methyl hydrogen (R)-3-methylglutarate, (R)-3.A precursor for (S)-1, i.e. (S)-3-methyloctanoic acid, (S)-4, has been also prepared in 84 percent yield and over 96 percent enantiomeric purity by the BF3-mediated 1,4-addition of n-pentylcopper to (-)-8-phenylmenthyl crotonate, 15, followed by saponification.The enantiomeric purities of methyl (R)-3-methyloctanoate, (R)-7, and (S)-3-methyl-1-octanol, (S)-8, have been determined by converting these compounds into (R)- and (S)-3-methyloctanoic acid, (R)-4 and (S)-4, respectively, followed by GLC analysis of the corresponding 1-(1-naphthyl)ethylamides obtained from nearly optically pure (R)-1-(1-naphthyl)ethylamine.

SYNTHESIS OF THE TWO ENANTIOMERS OF THE SEX PHEROMONE OF DIABROTICA UNDECIMPUNCTATA HOWARDI AND OF CHIRAL PRECURSORS OF OTHER PHEROMONES STARTING FROM ENENTIOMERICALLY PURE METHYL HYDROGEN (R)-3-METHYLGLUTARATE

Readily available methyl hydrogen (R)-3-methylglutarate (2) is a useful chiral building block for the synthesis of several biologically active compounds.Enantiomerically pure (R)-2 has been employed to synthesize stereospecifically each of the two enantiomers, 1a and 1b, of 10-methyl-2-tridecanone,the sex pheromone of the southern corn rootworm, Diabrotica undecimpunctata howardi Barber.Compound (R)-2 has been also used to prepare 99percent optically pure (R)-3-methyl-1-pentanol (6) and enantiomerically pure (R)-5-methyl-i-tricosyne (7).These compounds are useful building blocks suitable for the further elaboration to other chiral insect pheromones.