• Title/Summary/Keyword: Epoxide

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Total Synthesis of Sufentanil

  • Shin, Dong-Yun;Ryu, Jae-Sang;Hyun, Soon-Sil;Park, Hyun-Ju;Jeon, Ra-Ok;Suh, Young-Ger
    • Archives of Pharmacal Research
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    • v.22 no.4
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    • pp.398-400
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    • 1999
  • Sufentanil, a potent anilidopiperidine analgesic, was synthesized from a simple thiophenylethylamine via six sequence. The key parts of this synthesis involved an efficient construction of thiophenylethylpiperidone by aminomethano desilylation-cyclization followed by Swern oxidation and a direct regioselective N-nucleophilic spiral epoxide cleavage with aniline promoted by Lewis acids.

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Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents

  • Cha, Jin Soon
    • Journal of Integrative Natural Science
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    • v.5 no.2
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    • pp.91-99
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    • 2012
  • A newly-devised Meerwein-Ponndorf-Verley (MPV) reagents, such as diisobutylacetoxyalanes and diisobutylmethanesulfonylalanes, achieved a clean conversion of unsymmetrical epoxides to the corresponding less substituted alcohols. This review covers the recent developments for such a regiospecific ring-opening reaction of epoxides.

The chemical structure of betulafolianediol (Betulafolianediol의 산학구조)

  • 지형준
    • YAKHAK HOEJI
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    • v.18 no.1
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    • pp.11-19
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    • 1974
  • A new dammarane-type triterpenoid, betulafolianediol, $C_{30}$H$_{52}$O$_{3}$, mp $165^{\circ}$[${\alpha}$]$_D$^{20}=+$20^{\circ}$, was isolated form the unsaponifiable fraction of leves of Betula latifalia $K_{OMAROV}$ (Betulaceae). From the spectral data of the betulafolianediol and its derivatives, betulafolianediol monoacetate (II) and betulafolianediol monoketone, the structure of betulafolianediol was provide to be 3${\alpha}$, 25-dioxy-dammarane-20[S]->24 [S]-epoxide.

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Cure Mechanism of DGEBA/MDA/SN System

  • Shim, Mi-Ja;Kim, Seong-Uk
    • Korean Journal of Materials Research
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    • v.3 no.3
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    • pp.272-275
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    • 1993
  • To modify the toughness of epoxy for matrix, succinonitrile(SN) was introduced to diglycidy1 ether of bisphenol-A (DGEBA)/methylene dianiline(MDA)system. Cure reaction mdchanism of the DGEBA/MDA/SN system was strdied through Fourier transform infrared(FT-IR) spectrometry. As a result, the reaction of nitrile group of SN with secondary amine and with hydroxy1 group prevented the reaction of hydroxy1 group with epoxide group from crossoinding. Nitrile groups produced amide group by reacting with hydroxy1 groups and made a lowered crosslind density in chain networks.

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Synthesis of Novel 9-Fluoroanthracycline Derivatives

  • Rho, Young S.;박시호;Kim, Sun Y.;조인호;이철현;정채준;Kang, Heun S.
    • Bulletin of the Korean Chemical Society
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    • v.19 no.1
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    • pp.74-78
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    • 1998
  • Synthesis of novel 9-fluoroanthracyclines carrying L-fucose as a sugar component is described. Compound 3 containing a fluorine at the C-9 position was synthesized from an epoxide 2 and HF/Pyr (7 : 3). Bromination and hydrolysis of compound 3 resulted in synthesis of an aglycone, 9-fluoroanthracyclinone 6. The α-(1b) and β -anomers (1a) of the final product were obtained in high yields by a coupling reaction with the L-fucose.

Synthesis and Reaction of Novel Tricyclic Dynemicin A Models with Methyl Group

  • 류훈한;홍용표
    • Bulletin of the Korean Chemical Society
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    • v.17 no.9
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    • pp.831-835
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    • 1996
  • New dynemicin A mimics with methyl group 2a and 2b were synthesized, and acid-induced hydrolyzed to see an electronic effect of substituent for epoxide opening. The model 2a with methyl group at C3 position was more rapidly transformed to diol 16a than 2b with methyl group at C2. This result suggests that any substituent at C3 position plays more important role than any substituent at C2 position in the dynemicin A mimic activation.