ChemInform Abstract: OPTICALLY ACTIVE VINYL SULFIDES, SYNTHESIS, PROPERTIES, AND RELATIONSHIP BETWEEN OPTICAL ROTATORY POWER AND OPTICAL PURITY

Chiellini, Elisabetta E.; Marchetti, Mauro; Salvadori, Piero; Lardicci, L.

doi:10.1002/chin.197424220

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“…− [α] D 25 = +4.17 (neat), ref. [α] D 25 = +3.98 (neat),42 [α] D 25 = +4.00 (neat) 43. − 1 H NMR: δ = 0.91 (t, 3 H, J = 7.4 Hz), 1.01 (d, 3 H, J = 6.6 Hz), 1.19−1.78 (m, 3 H), 3.33 (dd, 1 H, J = 6.0 and 9.8 Hz), 3.40 (dd, 1 H, J = 5.2 and 9.8 Hz).…”

Section: Methodsmentioning

confidence: 99%

Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

et al. 2001

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All sixteen stereoisomers of 3,7,11‐trimethyl‐2‐tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallén) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis‐3,4‐dimethyl‐γ‐butyrolactone with each of the four pure stereoisomers of 1‐lithio‐2,6‐dimethyloctanes. The four corresponding alcohols were obtained by lipase‐catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)‐ or (2R/S,6R)‐2,6‐dimethyl‐1‐octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11‐trimethyl‐2‐tridecanol was also prepared.

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Section: Methodsmentioning

confidence: 99%

Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

et al. 2001

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ChemInform Abstract: OPTICALLY ACTIVE VINYL SULFIDES, SYNTHESIS, PROPERTIES, AND RELATIONSHIP BETWEEN OPTICAL ROTATORY POWER AND OPTICAL PURITY

Abstract: Aus den optisch aktiven Alkoholen (I) erhält man durch Reaktion mit PBr3/Pyridin die Alkylbromide (II), die mit Thioharnstoff (III) in Wasser zu den Isothiuroniumsalzen (IV) reagieren.

Cited by 1 publication

References 0 publications

Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine SawflyMicrodiprion pallipes(Hymenoptera: Diprionidae)

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