Selective monotetrahydropyranylation of 1,n-diols catalyzed by aqueous acids

Nishiguchi, Takeshi; Hayakawa, Seiji; Hirasaka, Yoshihiro; Saitoh, Masahiko

doi:10.1016/s0040-4039(00)01742-1

Cited by 18 publications

(11 citation statements)

References 5 publications

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“…1. Swern oxidation of monoTHP-protected (Nishiguchi et al, 2000) octane-1,8-diol (2) yielded aldehyde 3, which was chain-elongated by Wittig reaction using methyl triphenylphosphonium bromide (28% over three steps). Deprotection (67%) of resulting THP-protected 8-nonen-1-ol (4) followed by another Swern oxidation gave access to 8-nonenal (6), which was used in the next step without further purification.…”

Section: Resultsmentioning

confidence: 99%

Biological Activity of the Larval Secretion of Chilecomadia valdiviana

et al. 2011

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The carpenter worm, Chilecomadia valdiviana (Lepidoptera: Cossidae), is a polyphagous insect native to Chile that is associated with trees and bushes, including economically important species such as eucalyptus, avocado, and apples. We used a Y-olfactometer to analyze the olfactory responses of larvae to conspecific larvae, hexane extracts of larvae, and synthetic samples of the major components present in the extract (i.e., (Z)-5,13-tetradecadienyl acetate, (Z)-5-tetradecenyl acetate, and dodecyl acetate). The results obtained provide empirical evidence that (Z)-5,13-tetradecadienyl acetate is used as an aggregation pheromone by the larvae. The results are discussed in view of the existing information.

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Section: Resultsmentioning

confidence: 99%

Biological Activity of the Larval Secretion of Chilecomadia valdiviana

et al. 2011

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“…The first application was the protection of an amino functional group, as shown in Fig. 3, 7) which demonstrated the usefulness of the filter attached to the reaction flask and the dropwise addition of reagents from the reagent unit. As an example of the protection of only one amino group of a compound containing two equivalent amino groups, the di-amino compound, ethylenediamine, was protected with a single t-butoxycarbonyl (Boc) group.…”

Section: Resultsmentioning

confidence: 99%

“…The organic layer was concentrated in vacuo to give 1.49 g of (2-amino-ethyl)-carbamic acid t-butyl ester (isolated yield, 93%; cf. yield in literature, 7) 90%). Synthesis of 5-(Tetrahydro-pyran-2-yloxy)pentan-1-ol This reaction was carried out as shown in Fig.…”

Section: Methodsmentioning

confidence: 91%

Development and Application of a Solution-Phase Automated Synthesizer, 'ChemKonzert'

Machida¹,

Hirose²,

Fuse

et al. 2010

Chem. Pharm. Bull.

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In this paper we describe the development of a fully-automated solution-phase synthesizer, 'ChemKonzert' that can be used to prepare a wide variety of organic compounds. The automated synthesizer is ingeniously designed to perform most of the chemical reactions currently used by synthetic organic chemists and utilizes a centrifugal separator to efficiently achieve liquid-liquid extraction. The design of the hardware and software will be described in this paper, and several examples of organic reactions will also be presented as applications of the apparatus.

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“…Reactions with airor water-sensitive reagents were carried out in oven-dried glassware under Ar. 1 H-and 13 C-NMR spectra were recorded on a Varian INOVA-400 (400 and 100.5 MHz, Synthesis of 2-methylhexacosane 12-(Tetrahydropyran-2-yloxy)-dodecan-1-ol (2) This compound was made by a modification of the method of Nishiguchi et al (2000). Thus, 1,12-dodecanediol 1 (50.0 g, 247 mmol) was dissolved in a mixture of hexane (580 ml), dihydropyran (62.40 g, 741 mmol) and dimethylsulfoxide (21 ml).…”

Section: Synthesis Of 2-methylhexacosane and 2-methyloctacosanementioning

confidence: 99%

“…In the first (Fig. 3), 1,12-dodecanediol 1 was mono-protected with 3,4-dihydropyran (DHP) to give 2 in 81% isolated yield (Nishiguchi et al, 2000), and the remaining hydroxyl group then was converted to the tosylate 3 (75%). Coupling of tosylate 3 with 3-methylbutyl magnesium bromide with Li 2 CuCl 4 catalysis installed the methyl branch, giving 15-methyl-1-(tetrahydropyran-2-yloxy)-hexadecane 4 (95%), which was deprotected in acidic MeOH to give 15-methyl-hexadecan-1-ol 5.…”

Section: Identification Of Cuticular Hydrocarbonsmentioning

confidence: 99%

First Contact Pheromone Identified for a Longhorned Beetle (Coleoptera: Cerambycidae) in the Subfamily Prioninae

et al. 2010

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Little is known of the reproductive behavior of longhorned beetles (Coleoptera: Cerambycidae) in the subfamily Prioninae. Mallodon dasystomus (Say), the hardwood stump borer, is a widely distributed prionine that is native to the southern U.S. Here, we explored the chemically-mediated mating behavior of M. dasystomus, and tested the hypothesis that males recognize females by a contact pheromone. In mating bioassays, all males tested attempted to mate with females only after contacting females with their antennae. Moreover, all males attempted to mate with solvent-washed dead females treated with as little as 0.15 ± 0.03 female equivalents of conspecific cuticular extracts, confirming that compounds on the cuticle of females are essential for mate recognition. Cuticular hydrocarbon profiles of females contained 13 compounds that were not present in profiles of males. Among the female-specific compounds, two co-dominant methyl-branched alkanes, 2-methylhexacosane (2Me-C(26)) and 2-methyloctacosane (2Me-C(28)), accounted for 17% of the total hydrocarbons. Our strategy for identifying the contact pheromone was to synthesize and test the bioactivity of female specific compounds, starting with the most abundant. In bioassays, males displayed mating behavior in response to synthetic 2Me-C(26) and 2Me-C(28) when tested individually. Furthermore, when these compounds were tested in combination, they elicited the full progression of mating behaviors, suggesting that 2Me-C(26) and 2Me-C(28) make up the contact pheromone. These findings are further evidence of the critical role of contact pheromones in mating systems of longhorned beetles.

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Selective monotetrahydropyranylation of 1,n-diols catalyzed by aqueous acids

Cited by 18 publications

References 5 publications

Biological Activity of the Larval Secretion of Chilecomadia valdiviana

Biological Activity of the Larval Secretion of Chilecomadia valdiviana

Development and Application of a Solution-Phase Automated Synthesizer, 'ChemKonzert'

First Contact Pheromone Identified for a Longhorned Beetle (Coleoptera: Cerambycidae) in the Subfamily Prioninae

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