• Title/Summary/Keyword: Deprotection

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Identification of Homoserine Lactone Derivatives Using the Methionine Functionalized Solid Phase Synthesis by Gas Chromatography/Mass Spectrometry

  • Moon, Hong-Sik
    • Archives of Pharmacal Research
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    • v.27 no.1
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    • pp.25-30
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    • 2004
  • Combinatorial homoserine lactone mixtures and individual products were obtained from the methionine-functionalized resin in solid-phase synthesis. The four-step process consisting of a coupling step of an N-Fmoc-L-methionine, deprotection of N-Fmoc group, N-coupling with a carboxylic acid, and cleavage reaction through a polymer supported strategy is described. Gas chromatography-mass selective detector (GC-MSD) techniques provide the most powerful methods for identifying both the combinatorial mixtures and individual products.

O-Alkylation Using Ag2O; Synthesis of Novel 4-Alkyloxy-2-phenylcarboxamidyl-1-tosylpyrrolidines (산화은을 이용한 O-알킬화 반응; 새로운 4-알킬옥시-2-페닐카복사미딜-1-토실피롤리딘 유?체의 합성)

  • Park, Myeong Suk
    • Journal of the Korean Chemical Society
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    • v.45 no.6
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    • pp.549-554
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    • 2001
  • For the development of new COX-2 inhibitor, novel compound were synthesized through induction an arylsulfonyl group to 1-position, an arylcarboxamidyl group to 2-position and an alkyl group to 4-position of L-proline. We started from 4-hydroxy-L-proline, the 4-methylphenylsulfonyl of 1-position was introduced through N-tosylation and the carboxylic acid group was protected by esterification. We sucessfully converted to a various derivatives 4b-d for O-alkyl-(or aralkyl)ation of 4-position using silver oxide as catalysis. The 4-alkyloxy-1-tosyl L-prolines 5b-d were synthesized through base-hydrolysis for the deprotection of carboxylic acid. Final compound 1,2,4-substituted pyrrolidines, 4-alkyloxy-2-phenylcarboxamidyl-1-tosyl pyrrolidines 6a-d were synthesized through the condensation of arylamine with 3 and 5b-d using DCC.

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Synthesis of Ionic Elastomer Based on Styrene-Butadiene Rubber Containing Methacrylic Acid (Methacrylic Acid가 도입된 Styrene-Butadiene Rubber를 기반으로 한 Ionic Elastomer 합성)

  • Kim, Ki-Hyun;Lee, Jong-Yeop;Choi, Joon-Myeong;Kim, Hee-Jung;Seo, Byeongho;Kim, Bong-Soo;Kwag, Gwang-Hoon;Paik, Hyun-Jong;Kim, Wonho
    • Elastomers and Composites
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    • v.48 no.1
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    • pp.46-54
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    • 2013
  • A new terpolymer, styrene-butadiene-benzyl methacrylate copolymer (BzMA-SBR) was synthesized by emulsion polymerization. After polymerization, XSBR ionomer was prepared by deprotection of benzyl group of BzMA through hydrolysis with NaOH. Carboxyl group contents can be controlled by changing the initial feed contents of BzMA. Structure of BzMA-SBR and XSBR were characterized by FTIR, $^1H$ NMR and DSC.

Selective Synthesis of 1'(α),2'(β)-C-Dimethyl Carbocyclic Adenosine Analogue as Potential anti-HCV Agent

  • Li, Hua;Lee, Won-Jae;Yoo, Jin-Cheol;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.30 no.9
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    • pp.2039-2042
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    • 2009
  • As a part of an ongoing effort to discover inhibitors of the Hepatitis C Virus RNA replication, we describe here the first synthetic route of 1'($\alpha$),2'($\beta$)-C-dimethyl carbocyclic adenine analogue. The key intermediate cyclopentenyl alcohol 8($\alpha$) was prepared from aldehyde 4 using ring-closing metathesis (RCM) as a key reaction. Coupling of 8($\alpha$) with nucleosidic base via the regioselective Mitsunobu reaction followed by stereoselective dihydoxylation and deprotection afforded the target carbocyclic adenine analogue 12.

Synthesis and Optical Properties of Poly(hydroxyphenylbenzoxazole): A Colorimetric and Fluorescent Sensor for Ionic Species

  • Lee, Jin-Koo;Kim, Tae-Hyun;Kim, Young-shin;Gang Li;Park, Won-Ho;Lee, Taek-Seung
    • Proceedings of the Korean Fiber Society Conference
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    • 2003.10a
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    • pp.23-24
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    • 2003
  • We synthesized a poly[2-(2'-hydroxyphenyl) benzoxazole] under the two step procedures of Suzuki coupling polymerization with corresponding monomers followed by the deprotection of benzyl group. The polymer in DMF solution is applicable to colorimetric sensing fluoride anion, which shows a color change from colorless to yellow. High sensitivity to fluoride anion compared to other anions such as phosphate, chloride, and sulfate is ascribed to the high coordination ability of the 2-(2'-hydroxy phenyl)benzoxazole moiety in the polymer chain. Emission shift by metal cations, which can be applied to fluorescent sensing w as also observed in the polymer solution.

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Silica Sulfuric Acid/Wet $SIO_2$as a Novel System for the Deprotection of Acetals by Using Microwave Irradiation under Solvent Free Conditions (무용매 조건하에서 황산/젖은 $SIO_2$와 마이크로웨이브를 이용한 아세탈의 새로운 탈보호기 방)

  • BiBi Fathemeh, Mirjalili; Mohammad Ali, Zolfigol;Abdolhamid, Bamoniri
    • Journal of the Korean Chemical Society
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    • v.45 no.6
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    • pp.546-548
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    • 2001
  • Neat chlorosulfonic acid reacts with silica gel to give silica sulfuric acid in which sulfuric acid is immobilized on the surface of silica gel via covalent bond. A combination of silica sulfuric acid and wet SiO$_2$ was used as an effective deacetalizating agent for the conversion of acetals to their corresponding carbonyl derivatives by using microwave irradiation under solvent free conditions.

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Synthesis and $\beta$-lactamase inhibitory activity of 6-exomethylene penamsulfone derivatives - II (Synthesis of 6-exomethylene penamsulfone derivatives)

  • Yim, Chul-Bu;Youm, Jeong-Rok;Im, Chae-Uk;Park, Hee-Suk;Oh, Jeong-Suk;Park, Kye-Hwan
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1996.04a
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    • pp.160-160
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    • 1996
  • $\beta$-Lactam계 항생제 내성균의 문제를 해결할 수 있는 $\beta$-lactamase억제제의 개발을 위해서, cephalosporinase에 특히 높은 억제활성을 갖는 새로운 6-exomethylene penamsulfones 화합물을 합성하였다. Dibromopenamsulfone과 thioalkyl triazole-4-carboxaldehyde을 반응시키고, acetic anhydride와 Zn으로 처리하여 E-form과 Z-form의 6-exomethylene penam sulfones을 합성하였다. 이것을 AlCl$_3$으로 deprotection시킨 후, NaOH로 처리하여 6-exomethylene penamsulfone의 Na-salt form으로 목적물질을 합성하였다.

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Synthesis and $\beta$-lactamase inhibitory activity of 6-exomethylene penamsulfone derivatives-II (Synthesis of 6-exomethylene penamsulfone derivatives)

  • Park, Hee-Suk;Yoon, Sang-Bae;Chaeuk Im;Yim, Chul-Bu
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1997.04a
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    • pp.71-71
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    • 1997
  • $\beta$-lactamase를 생성하는 균들이 $\beta$-lactam계 항생제를 분해하여 불활성화 시키므로 이를 해결하기 위하여 그 효소에 대하여 억제활성을 나타내는 새로운 6-exomethylenepenamsulfone화합물들을 합성하였다. Dibromopenamsulfone과 heterocyclic ring을 함유한 thioethyl triazole-4-carboxaldehyde를 반응시키고, acetic anhydride와 Zn으로 처리하여 E-form과 Z-form의 6-exomethylene penmsulfones을 합성하였다. 이것을 AlCl$_3$로 처리하여 deprotection시킨 후, NaHCO$_3$로 처리하여 6-exomethylene penam sulfones의 Na-salt의 형태로 목적물질을 합성하였다.

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EXPLORATORY PHOTOCHEMICAL STUDY ON THE o-NITROBENZYLSULFONYL DERIVATIVES

  • Chang, Sun-Ki
    • Journal of Photoscience
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    • v.1 no.1
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    • pp.67-68
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    • 1994
  • INTRODUCTION : The photochemistry of nitro chromophore has been the subject of intense study only in recent years. Unlike the carbonyl functional group, of which the photochemistry has been quite extensively studied and fairly well understood, as a result of excellent work done by numerous physical and organic photochemists alike, the nature of photochemistry of nitro group has only recently been systematically explored. The photochemistry of nitro group exhibits general features of the photochemistry of the carbonyl groups such as hydrogen abstraction by the diradical species generated from the n-$\pi$$^*$ excited state of the nitro group. Other photochemical pathways common to the carbonyl group such as the biradical intermidiate formation, photocycloelimination, and cydoaddition reactions are also open for the nitro group. Of all the photochemical reactions of the nitro group mentioned above, hydrogen abstraction by the n-$\pi$$^*$ excited state of the nitro group has drawn much attention by synthetic organic chemists and polymer chemists. In the field of organic synthesis, above mintioned photochemical reaction has been utilized in the photoprotection-deprotection chemistry.

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Synthesis of 7-Arylidene Cephalosporanates for ${\beta}-lactamase$ Inhibitor (${\beta}-Lactamase$ 억제작용이 기대되는 7-Arylidene Cephalosporanate 유도체의 합성)

  • Lee, Jong-Min;Yim, Chul-Bu;Im, Chae-Uk
    • YAKHAK HOEJI
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    • v.52 no.4
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    • pp.311-315
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    • 2008
  • The synthesis of 7-arylidene cephalosporanates for ${\beta}-lactamase$ inhibitor was described. The reactions of substituted benzyl halides $[1]{\sim}[3]$ with triphenylphosphine gave triphenylphcsphonium chlorides $[4]{\sim}[6]$. These phosphonium salts were treated with n-butyllithium to give ylides, which were reated with 7-oxocephalosporanate [7] by Wittig reaction to afford the 7-exomethylene cephalosporanates $[8]{\sim}[10]$. These cephalosporanates were oxidized to cephalosporanate sulfones $[11]{\sim}[13]$ with mCPBA. The deprotection of benzhydryl cephalosporanate $[8]{\sim}[13]$ with $AlCl_3$ and $NaHCO_{3}$ gave sodium salts of 7-arylidene cephalosporanates $[14]{\sim}[19]$.