Updated on 2024/04/16

写真a

 
SATO Eisuke
 
Organization
Faculty of Environmental, Life, Natural Science and Technology Assistant Professor
Position
Assistant Professor
External link

Degree

  • 博士(理学) ( 2018.3   慶應義塾大学 )

Research History

  • 岡山大学大学院   助教

    2020.4

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Papers

  • Electrochemical Coupling Reactions Using Non‐Transition Metal Mediators: Recent Advances

    Koichi Mitsudo, Yasuyuki Okumura, Eisuke Sato, Seiji Suga

    European Journal of Organic Chemistry   2023.12

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.202300835

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  • Alkynylation of Aldehydes Initiated by Cathodic Reduction

    Eisuke Sato, Mayu Fujii, Koichi Mitsudo, Seiji Suga

    ChemElectroChem   2023.12

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/celc.202300499

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  • Anodic Dehydrogenative Aromatization of Tetrahydrocarbazoles Leading to Carbazoles

    Eisuke Sato, Ayaka Yukiue, Koichi Mitsudo, Seiji Suga

    Organic Letters   2023.7

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.3c01914

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  • Electrochemical Synthesis of Sultone Derivatives via Dehydrogenative C–O Bond Formation International journal

    Koichi Mitsudo, Yasuyuki Okumura, Kotaro Yohena, Yuji Kurimoto, Eisuke Sato, Seiji Suga

    Organic Letters   25 ( 19 )   3476 - 3481   2023.5

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    Language:English   Publishing type:Research paper (scientific journal)  

    Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

    DOI: 10.1021/acs.orglett.3c01062

    PubMed

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  • Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator

    Koichi Mitsudo, Keisuke Shigemori, Taro Shibata, Hiroki Mandai, Eisuke Sato, Seiji Suga

    Synthesis   2023.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag {KG}  

    <jats:p>An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br− in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.</jats:p>

    DOI: 10.1055/a-2034-9821

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  • Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions Reviewed

    Eisuke Sato, Gaku Tachiwaki, Mayu Fujii, Koichi Mitsudo, Takashi Washio, Shinobu Takizawa, Seiji Suga

    Organic Process Research & Development   2023.1

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.oprd.2c00267

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  • Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides

    Yasuyuki OKUMURA, Eisuke SATO, Koichi MITSUDO, Seiji SUGA

    Electrochemistry   2023

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    Publishing type:Research paper (scientific journal)   Publisher:The Electrochemical Society of Japan  

    DOI: 10.5796/electrochemistry.23-67078

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  • Preface for the 67th Special Feature “Revolutionizing Synthetic Organic Chemistry by Electrosynthesis

    Naoki SHIDA, Eisuke SATO

    Electrochemistry   2023

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.5796/electrochemistry.23-67113

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  • Cathodic N–O Bond Cleavage of N-Alkoxy Amide

    Eisuke SATO, Sayaka OGITA, Koichi MITSUDO, Seiji SUGA

    Electrochemistry   2023

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    Publishing type:Research paper (scientific journal)   Publisher:The Electrochemical Society of Japan  

    DOI: 10.5796/electrochemistry.23-67079

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  • Electrochemical Synthesis of Dibenzothiophenes via Intramolecular C–S Cyclization with a Halogen Mediator

    Koichi Mitsudo, Yuri Tachibana, Eisuke Sato, Seiji Suga

    Organic Letters   24 ( 46 )   8547 - 8552   2022.11

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.2c03574

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  • A Facile Access to Spirooxindoles by Halogen-Mediated Electrochemical Semi-pinacol Rearrangement Reviewed

    Eisuke SATO, Sae KANGAWA, Koichi MITSUDO, Seiji SUGA

    Chemistry Letters   51 ( 11 )   1067 - 1069   2022.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.220368

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  • Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility Reviewed

    Koichi Mitsudo, Haruka Inoue, Yuta Niki, Eisuke Sato, Seiji Suga

    Beilstein Journal of Organic Chemistry   18   1055 - 1061   2022.8

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Beilstein Institut  

    Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C).

    DOI: 10.3762/bjoc.18.107

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    Other Link: https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-18-107.pdf

  • Electro-oxidative Trimerization of 1,2-Dimethoxybenzene: Reductive Workup Strategy and Alternating Current Electrolysis to Peel off the Precipitated Radical Cation Ion Pair Reviewed

    Eisuke Sato, Yuta Niki, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   51 ( 6 )   629 - 632   2022.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.220112

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  • Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis Reviewed

    Eisuke Sato, Mayu Fujii, Hiroki Tanaka, Koichi Mitsudo, Masaru Kondo, Shinobu Takizawa, Hiroaki Sasai, Takeshi Washio, Kazunori Ishikawa, Seiji Suga

    The Journal of Organic Chemistry   86 ( 22 )   16035 - 16044   2021.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

    DOI: 10.1021/acs.joc.1c01242

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  • Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling Reviewed

    Nina Vierengel, Leander Geske, Eisuke Sato, Till Opatz

    The Chemical Record   21 ( 9 )   2344 - 2353   2021.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/tcr.202100078

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/tcr.202100078

  • Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes Reviewed

    Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

    Organic Letters   23 ( 11 )   4322 - 4326   2021.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.1c01256

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  • Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator Reviewed

    Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

    Organic Letters   23 ( 8 )   3120 - 3124   2021.4

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.1c00807

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  • Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products Reviewed

    Till Opatz, Leander Geske, Eisuke Sato

    Synthesis   52 ( 19 )   2781 - 2794   2020.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

    Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.

    1 Introduction

    2 Shono-Type Oxidation

    3 C–N/N–N Bond Formation

    4 Aryl–Alkene/Aryl–Aryl Coupling

    5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes

    6 Spirocycles

    7 Miscellaneous Transformations

    8 Future Prospects

    DOI: 10.1055/s-0040-1707154

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  • Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria Reviewed

    Eisuke Sato, Maho Morita, Haruo Ogawa, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Satoshi Ōmura, Arihiro Iwasaki, Kiyotake Suenaga

    Bioorganic & Medicinal Chemistry Letters   28 ( 3 )   298 - 301   2018.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2017.12.050

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  • Total Synthesis of Biselyngbyaside Reviewed

    Eisuke Sato, Miho Sato, Yurika Tanabe, Naoya Nakajima, Akifumi Ohkubo, Kiyotake Suenaga

    The Journal of Organic Chemistry   82 ( 13 )   6770 - 6777   2017.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.7b00905

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  • Total Synthesis of Biselyngbyolide B Reviewed

    Eisuke Sato, Yurika Tanabe, Naoya Nakajima, Akifumi Ohkubo, Kiyotake Suenaga

    Organic Letters   2016.5

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.6b00660

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  • Total Synthesis of Biselyngbyolide A Reviewed

    Yurika Tanabe, Eisuke Sato, Naoya Nakajima, Akifumi Ohkubo, Osamu Ohno, Kiyotake Suenaga

    Organic Letters   2014.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol500996n

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Awards

  • 塩野義製薬 研究企画賞

    2021.12   有機合成化学協会  

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  • 日本化学会第98春季年会 学生講演賞

    2018.3  

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Research Projects

  • 陽極酸化による電子移動触媒型化学反応プロセスの開発

    Grant number:23K13748  2023.04 - 2026.03

    日本学術振興会  科学研究費助成事業 若手研究  若手研究

    佐藤 英祐

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

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  • 機械学習を利用した有機電解合成反応の効率的最適化

    2021.10 - 2024.03

    科学技術振興機構  JST戦略的創造研究推進事業 ACT-X 

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    Authorship:Principal investigator 

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  • An anodic oxidation of indole for a new transformation

    Grant number:20K22534  2020.09 - 2022.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Research Activity Start-up

    Sato Eisuke

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    Grant amount:\2860000 ( Direct expense: \2200000 、 Indirect expense:\660000 )

    The electron rich property of the indole skeleton makes it easy to oxidize under mild conditions. In this research, the anodic oxidation of indole compounds were performed. The use of lithium bromide as a halogen mediator enables the anodic transformation, and two type of tricyclic indole compounds showed different skeletal transformations.

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  • ビセリングビアサイド類の合成と生物活性

    Grant number:17J03602  2017.04 - 2019.03

    日本学術振興会  科学研究費助成事業 特別研究員奨励費  特別研究員奨励費

    佐藤 英祐

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    Grant amount:\1900000 ( Direct expense: \1900000 )

    本年度は、ビセリングビアサイド類をより効率良く合成するために、合成ルートの改善を行った。
    これまではトリメチレングリコールを出発原料とした合成ルートを用いてビセリングビアサイド類の全合成を行なっていたが、新たな合成計画においては不斉点を既に有するRocheエステルを出発原料として用いた。既に不斉点を有する化合物を用いることで、工程数を削減することができた。さらに、ヨウ化ビニル部分を合成の序盤で構築することによって、保護基の脱着や酸化段階の調整を減らすことが可能となった。さらに、以前の手法において毒性の高く高価な塩化クロムを大過剰用いる必要があったが、新しい合成ルートにおいてはヨウ化ビニルへの変換において安価なシュワルツ試薬を用いる手法が適用可能であり、大量合成を目指す上で重要性が高い。
    以前の合成手法での問題点としてあげられていた、不斉補助基を用いる方法についての改善を行った。不斉補助基を用いる反応は、新たな不斉点構築を行う際に選択性と収率の双方から信頼性の高い手法であったが、等量の不斉補助基を用いる点でアトムエコノミーの観点から問題視されていた。本研究においては、アルデヒドに対して不斉補助基を用いた立体選択的アルドール反応の代わりに、イリジウム触媒を用いた立体選択的なアリル化反応を適用することで問題の解決をはかった。アリル化反応の立体選択性は非常に高く目的の立体化学を有する化合物を与えることがわかったが、反応の進行が途中で止まってしまうことがわかった。本原因については現在調査中である。

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Class subject in charge

  • Green and Sustainable Chemical Processes (2023academic year) Late  - 水3~4

  • Experiment for Chemistry and Biotechnology 1 (2023academic year) 1st and 2nd semester  - 月5~8

  • Experiment for Chemistry and Biotechnology 1 (2023academic year) 1st and 2nd semester  - 木5~8

  • Experiment for Chemistry and Biotechnology 2 (2023academic year) Fourth semester  - 月5~8

  • Synthetic Process Chemistry (2023academic year) Late  - その他

  • Synthetic Chemistry Experiment 1 (2023academic year) Fourth semester  - 月5~8

  • Synthetic Organic Materials (2023academic year) Late  - その他

  • Basic Experiments in Chemistry (2023academic year) 1st and 2nd semester  - 月5~8

  • Basic Experiments in Chemistry (2023academic year) 1st and 2nd semester  - 木5~8

  • Laboratory Work and Practice on Basic Engineering (2023academic year) 1st and 2nd semester  - 火5~8

  • Laboratory Work and Practice on Basic Engineering (2023academic year) 1st and 2nd semester  - 火5~8

  • Seminar on Applied Chemistry 1 (2023academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2023academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2023academic year) Year-round  - その他

  • Seminar in Advanced Chemistry (2023academic year) Other  - その他

  • Material Process Experiment 1 (2023academic year) Fourth semester  - 月5~8

  • Advanced Study (2023academic year) Other  - その他

  • Biotechnology experiment 1 (2023academic year) Fourth semester  - 月5~8

  • Frontier Synthetic Chemistry (2022academic year) Late  - 金1,金2

  • Experiment for Chemistry and Biotechnology 2 (2022academic year) Fourth semester  - 月5~8

  • Synthetic Chemistry Experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Internship in Applied Chemistry (2022academic year) Prophase  - その他

  • Laboratory Work and Practice on Basic Engineering (2022academic year) 1st and 2nd semester  - 火5~8

  • Laboratory Work and Practice on Basic Engineering (2022academic year) 1st and 2nd semester  - 火5~8

  • Seminar on Applied Chemistry 1 (2022academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2022academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2022academic year) Year-round  - その他

  • Material Process Experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Biotechnology experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Frontier Synthetic Chemistry (2021academic year) Late  - 金1,金2

  • Synthetic Chemistry Experiment 1 (2021academic year) Fourth semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Synthetic Chemistry Experiment 1 (2021academic year) Fourth semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Internship in Applied Chemistry (2021academic year) Prophase  - その他

  • Laboratory Work and Practice on Basic Engineering (2021academic year) 1st and 2nd semester  - 火5,火6,火7,火8

  • Laboratory Work and Practice on Basic Engineering (2021academic year) 1st and 2nd semester  - 火5,火6,火7,火8

  • Laboratory Work and Practice on Basic Engineering (2021academic year) 1st and 2nd semester  - 火5,火6,火7,火8

  • Seminar on Applied Chemistry 1 (2021academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2021academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2021academic year) Year-round  - その他

  • Synthetic Chemistry Experiment 1 (2020academic year) Fourth semester  - 月4,月5,月6,月7,木4,木5,木6,木7

  • Synthetic Chemistry Experiment 1 (2020academic year) Fourth semester  - 月4,月5,月6,月7,木4,木5,木6,木7

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