66050-75-7

Upstream product

• 137-32-6 (+/-)-2-methyl-1-butanol 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 616-16-0 (R)-2-Methyl-1-butanol 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 
• 130856-00-7 (R)-2-methyl-1-(2-tetrahydropyranyloxy)butane 
• 33204-48-7 (R)-2-methylbutanal 

Relevant academic research and scientific papers

Synthesis of the four possible stereoisomers of N-2′-methylbutyl-2-Methylbutylamide, the sex pheromone of the longhorn beetle Migdolus fryanus westwood

The four stereoisomers of N-2′-methylbutyl-2-methylbutylamide, the sex pheromone of the longhorn beetle Migdolus fryanus, an economically important pest of sugarcane in South America, were synthesized. The key intermediate 2-methylbutan-1-ol is commercially available only in its (S)-(-)-form. The (R)-(+)-enantiomer was obtained optically pure from methyl (S)-(+)-3-hydroxy-2-methylpropionate in five steps.

Highly stereoselective allylic ethylation with alkoxytitanacyclopropane reagents. Synthesis of (1R/S,7R)-1,7-dimethylnonyl propanoate, the Western corn rootworm sex attractant

Allylic ethylation of 2-((E)-dodec-2-en-4-yloxy)tetrahydro-2H-pyran with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide proceeds via a SN2′ pathway to afford (E)-3-methyltridec-4-ene with excellent syn-diastereoselecivity. This transformation is used as a key step in the synthesis of (1R/S,7R)-1,7-dimethylnonyl propanoate, the Western corn rootworm (Diabrotica virgifera virgifera) sex attractant.

Synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal: the common aggregation pheromone of flour beetles

The synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal 1 and 1a has been achieved connecting the chiral building block (R)-2-methyl-1-bromobutane 4 with (R)- and (S)-citronellol derivatives. The key intermediate 4 was obtained optically pure in five steps from methyl (S)-3-hydroxy-2-methylpropionate 2.

Absolute configuration of main chain of AAL-toxins

AAL-toxins TA1 1 and TA2 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1,3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthetic samples by comparison of their 500 MHz 1H-NMR spectra. The remaining stereocenters were determined by the comparison of 1H-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.

Predator - Prey Relationship between Navanax inermis and Bulla gouldiana : a Chemical Approach

Two new compounds, 5,6-dehydroaglajne-3 (9) and isopulo'upone (10), have been isolated and characterized, along with the already known niuhinone-B (7), from Navanax inermis and its prey Bulla gouldiana, firmly establishing on a chemical basis the predator - prey relationship between this pair of cephalaspidean opisthobranchs.The peculiarity of the metabolites and their structural analogy with other compounds isolated from other cephalaspidean molluscs assign a taxonomic relevance for them. Key words: Navanax inermis; Bulla gouldiana; cephalaspidean molluscs; polypropionates.