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• 84621-64-7 (2R,3S)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 78088-28-5 ethyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 66767-64-4 Sodium (2S,3S)-2-methyl-3-hydroxybutanoate 
• 84567-98-6 (2S,3S)-2-Methyl-3-hydroxybuttersaeure 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 110-87-2 3,4-dihydro-2H-pyran 
• 944357-52-2 (2S,3S)-2-Methyl-3-(tetrahydro-pyran-2-yloxy)-butyric acid methyl ester 
• 66767-60-0 methyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 84567-99-7 butyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 124990-50-7 butyl (-)-(3S)-3-hydroxy-2-methylenebutanoate 

Relevant academic research and scientific papers

Asymmetric syntheses of the sex pheromones of pine sawflies, their homologs and stereoisomers

We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis, their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e., 126. A total of 48 compounds, including acetates 78-101 and propanoates 102-125, have been synthesized. Our general approach towards these compounds originated from the commercially available chirons diethyl (S)- and (R)-malates, as well as ethyl (R)-3-hydroxybutanoate. The Seebach asymmetric methylation was employed in a key step to control additional configuration. Copyright

Enantioselectivity in odor perception synthesis and olfactory properties of the new tricyclic sandalwood odorant Fleursandol

The 3-methyl-4-(tricyclo[5.2.1.02,6]dec-4-en-8-ylidene)butan-2- ols (=Fleursandol; rac-10), a new class of sandalwood odorants, were synthesized in their enantiomerically pure forms by use of tricyclo[5.2.1.0 2,6]dec-4-en-8-ones 17 and ent-17 and (tetrahydro-2H-pyran-2-yl)- protected 4-bromo-3-methylbutan-2-ols 22 and ent-22 as starting materials (Schemes 2-4). Only four of 16 possible stereoisomers of rac-10 possess the typical, very pleasant, long-lasting sandalwood odor (Table 1). The (2S,3R,4E,1′R,2′R,6′R,7′R)-isomer ent-10a is by far the most important representative, with an odor threshold of 5 μg/l in H 2O.

Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica

Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.

Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates

(1S, 2R, 6RS)-1,2,6-Trimethyldecyl propionate, a lower homolog of the sex pheromone of known sawflies, strongly attracted Diprion nipponica, a popular species in Japan.

Preparation of Stereochemically Pure Sex Pheromone Components of the Pine Sawfly (Neodiprion sertifer) and Field Tests of the Synthetic Compounds

Stereochemically pure pheromone components of the pine sawfly, acetates of (2S,3S,7S)- and (2S,3R,7R)-3,7-dimethylpentadecan-2-ol, were prepared by an improved synthetic procedure.Mixtures of the newly prepared compounds were tested in the field (red pine forests in Hyogo and Nagano, Japan) for their attraction of Neodiprion sertifer.The maximum response was observed in mixtures of the ratio (2S,3R,7R)/(2S,3S,7S)-10-3: 1 to 10-4: 1.When the results are compared with those in Michigan, U.S.A., N. sertifer in Japan responded less specifically to certain blending ratios of diastereomers than in America.

Syntheses of the Sex-Attractant of Pine Sawfies

In order to establish the stereochemistry of the sex attractant of various species of pine sawflies, (2S,3R,7R)-, (2S,3R,7S)- and (2S,3S,7S)-2-acetoxy- and 2-propionyloxy-3,7-dimethylpentadecane were synthesized.The alcohol moiety of each pheromone was prepared by the coupling of Grignard reagent of C12 block with tosylate of C5 block.The C12 block, (R)- and (S)-1-bromo-2-methylundecane, were prepared from (R)-(+)-pulegone.The C5 block, (2R,3S)- or (2S,3S)-2-methyl-3-tetrahydropyranyloxy-1-(tosyloxy)butane, were derived from (2S,3S)- or (2R,3S)-2-methyl-3-hydroxy butyric acid prepared by the enantio-differentiating hydrogenation of methyl 2-methyl-3-oxobutyrate over the asymmetrically modified nickel catalyst.

SYNTHESIS OF THE SEX-ATTRACTANT OF PINE SAWFLIES (DIPRION SPECIES); (2S,3R,7R)- AND (2S,3R,7S)-3,7-DIMETHYLPENTADECAN-2-Ol

In order to establish the stereochemistry of the sex attractant of diprion species of pine sawflies, two candidate epimers, (2S,3R,7R)- and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol were synthesized by the coupling reaction of optically active C5 and C12 units.The C12 units, (R)-(-)- and (S)-(+)-1-bromo-2-methylundecane were prepared from (R)-(+)-pulegone.The C5 unit, (2R,3S)-2-methyl-3-tetrahydropyranoxy-1-tosyloxybutane was derived from (2S,3S)-2-methyl-3-hydroxybutyric acid prepared by the reported procedure.