An Effective Method for the Preparation of ω-Bromoalkanols from α,ω-Diols

Kang, Suk‐Ku; Kim, Won-Sup; Moon, Byoung-Ho

doi:10.1055/s-1985-31464

Cited by 109 publications

(44 citation statements)

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“…Wetherefore designate compoundll as isochainin. The other newpolyenes are close relatives: 14-Hydroxyisochainin (12), r-hydroxyisochainin (13), and r,14-dihydroxyisochainin (14). All compounds showed antifungal activity roughly comparable to that of amphotericin B in preliminary tests.…”

Section: Resultsmentioning

confidence: 90%

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Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl(Z)-16-phenylhexadec-9-enoate.

Rawlings

Harrison

et al. 1989

J. Antibiot.

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Section: Resultsmentioning

confidence: 90%

“…HPLCseparation (Waters C18 Radial Pak column, methanol -water (60 : 40), flow 1.00 ml/minute) of the supernatant afforded 14 (1.0 mg, retention time (tR) 8.37 minutes), 13 Table 1 for 13C NMR; positive ion FAB-MS (glycerol) m/z 665.69 (M-Na, C33H54O12 -Na), 642.48 (M, C33H54O12).…”

Section: -Phenylpentyl^-toluenesulfonate (4)mentioning

confidence: 99%

Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl(Z)-16-phenylhexadec-9-enoate.

Rawlings

Harrison

et al. 1989

J. Antibiot.

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“…Thus, hexane-1,6-diol (1) was partially brominated [8] to give the known compound 2 [9] which on silylation furnished 3. α-Alkylation of methyl acetoacetate (4) with 3 followed by alkaline hydrolysis gave the ketone 5. Its reduction with NaBH 4 afforded the key carbinol synthon 6 which was subjected to porcine pancreatic lipase (PPL) catalyzed trans-acylation under different conditions viz.…”

Section: Resultsmentioning

confidence: 99%

A Short and Efficient Synthesis of (R)-Phoracantholide I

Sharma

Chattopadhyay

1998

Molecules

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“…Although the method of Castro and co-workers in (6) for preparing azido-alcohols worked well in the synthesis of 2, the price of hexamethylphosphorous triamide (HMPT) coupled with the diminished yields upon the "scaling-up" of the reaction prompted the search for a new preparative route to 10-azido-l-decanol (see Scheme 1,5). Kang, Kim, and Moon describe a simple method for the preparation of o-bromo-alcohols from u,o-diols (7). Refluxing a mixture of an aliphatic diol with an equivalent of aqueous hydrogen bromide (48%) in benzene using a Dean-Stark apparatus provided high yields of the monobromo-alcohol.…”

Section: Synthesismentioning

confidence: 99%

“…The procedure used was that of Kang, Kim and Moon (7). To a solution of 1,lO-decanediol (17.4 g, 100 mmol) in benzene (200 mL) stirred in a 500 mL round bottom flask equipped with a Dean-Stark trap and a condenser was added hydrobromic acid (48%, 12.5 mL, 110 mmol).…”

Section: Synthesis Of 10-bromo-1-decanolmentioning

confidence: 99%

Synthesis, NMR and ultraviolet spectroscopy of [10] (N6,9)-6-aminopurinophane; calculation of the chemical shifts in the [n](N6,9)-6-aminopurinophane series

Capretta¹,

Bell²

1995

Can. J. Chem.

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Abstract:[10](N6,9)-6-Aminopurinophane was prepared via a Mitsunobu reaction involving 6-chloropurine and 10-azido-1-decanol. Reduction of the azido moiety to an amine allowed for subsequent cyclization to the cyclophane. N6-Nonyladenine, 9-nonyladenine, and N6,9-dinonyladenine were also prepared using the established chemistry. Heating the [10](N6,9)-6-aminopurinophane to 90°C allowed for a complete assignment of the proton and carbon spectra, while cooling the sample to -77°C revealed additional isomers likely due to the anti-syn isomerization about the N6-C6 bond. A variable temperature proton NMR study revealed a AG,' of 59.4 2 5.5 kJ mol-' associated with the interchange between the two major conformers. The ultraviolet spectra of the [n](N6,9)-6-aminopurinophane series show a bathochromic shift and a hypochromic effect in the transitions as the methylene chain length decreases (i.e., n = 10 to 9 to 8). The aminopurinophanes are used to assess the relative merits of a semi-empirical model that allows for the calculation of the chemical shifts of the methylene bridge protons.Key words: synthesis of heterocyclophanes, variable temperature NMR, cyclophane conformational analysis, ultraviolet spectroscopy, calculation of chemical shift.Resume : On a prepare le [10](N6,9)-6-aminopurinophane via une reaction de Mitsunobu impliquant la 6-chloropurine et le 10-azidodkcan-1-01. La rCduction de la portion azido en amine a permis de rCaliser la cyclisation subsCquente en cyclophane. On a aussi prCparC les N6-nonyladCnine, 9-nonyladCnine et N6,9-dinonyladenine utilisant des mCthodes chimiques bien Ctablies. Par chauffage du [10](N6,9)-6-aminopurinophane B 90°C, on a pu faire une attribution complbte des spectres RMN du proton et du carbone alors que son refroidissement B -77°C a rCvClC la presence d'isombres additionnels qui sont probablement dus B une isomCrisation anti-syn autour de la liaison N G C 6 . Une ttude des spectres RMN du proton B temperature variable a permis d'Ctablir qu'un AG,' de 39,4 ? 5,5 kJ mol-' est associC B l'interconversion entre les deux conformkres principaux. Les spectres ultraviolets de la sCrie des [tz](N6,9)-6-aminopurinophanes montrent qu'une diminution de la chaine mCthylCnique (lorsque n passe de 10, B 9 et B 8) est associCe B un dCplacement bathochrome et L un effet hypochrome dans les transitions. On a utilisC les aminopurinophanes pour Cvaluer les mCrites relatifs d'un modble semi-empirique qui permet de calculer les deplacements chimiques des protons des ponts mCthylbnes. ..Mots elks : synthkse d'hCterocyclophanes, RMN B temperature variable, analyse conformationnelle des cyclophanes, spectroscopie ultraviolette, calcul des dCplacements chimiques.[Traduit par la rCdaction] Introductionanisotropy about these purine and pyrimidine systems could aid in thegssignment of ;he heterobase protons ii the 'H NMRThe shift to lower frequency of the heterobase protons in cerspectra of large oligomers. Furthermore, this information tain oligonucleotides is a well-documented phenomenon (1 1.could ...

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An Effective Method for the Preparation of ω-Bromoalkanols from α,ω-Diols

Cited by 109 publications

References 0 publications

Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl(Z)-16-phenylhexadec-9-enoate.

Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl(Z)-16-phenylhexadec-9-enoate.

A Short and Efficient Synthesis of (R)-Phoracantholide I

Synthesis, NMR and ultraviolet spectroscopy of [10] (N6,9)-6-aminopurinophane; calculation of the chemical shifts in the [n](N6,9)-6-aminopurinophane series

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