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Development of mildly introducible PMB-substitute protecting groups and their application to the total synthesis

Research Project

Project/Area Number 15K21210
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Biomolecular chemistry
Synthetic chemistry
Research InstitutionKyushu University

Principal Investigator

Torikai Kohei  九州大学, 理学研究院, 助教 (20456990)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2015: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords保護基 / ナフチルメトキシメチル基 / 選択的除去 / NAPOM基 / BOM系保護基 / 加水素分解 / 1-NAP基 / 1-NAPOM基 / 酸化的除去
Outline of Final Research Achievements

In this work, "1-NAPOM" and "2-NAPOM" groups were developed as protecting groups, that work in the field of organic chemistry to suppress the reactivity of alcohols and thiols, and which can be cleaved in necessity. NAPOM groups are superior to the conventional members of benzyl and benzyloxymethyl families in that; i) it is orthogonally cleavable in the presence of benzyl and benzyloxymethyl groups; ii)it is removable in mild conditions (mildly basic, room temperature); and iii) NAPOMCl, an introducing reagent of NAPOM groups, is a stable and isolable solid, which can be stored and therefore be commerciallized.
Besides, it was revealed that these protecting groups can be applicable to the glyco- and peptide-chemistry. Therefore, NAPOM groups are expected to be useful tools in the field of organic chemistry, in the near future.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (19 results)

All 2018 2017 2016 2015 Other

All Journal Article (7 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 7 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (8 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 2 results)

  • [Journal Article] Synthesis of 6/6/6-Tricyclic Ether System via Achmatowicz and Intramolecular Oxa-Michael Reactions2018

    • Author(s)
      Yamamoto, H.; Torikai, K.; Ebine, M.; Oishi, T.
    • Journal Title

      Heterocycles

      Volume: in press Issue: 1 Pages: 158-162

    • DOI

      10.3987/com-17-s(t)10

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Syntheses of the WXYZ Ring of Maitotoxin and the HIJK Ring of Brevisulcenal-F2018

    • Author(s)
      Osato Naoya、Onoue Hisaaki、Toma Yoshiki、Torikai Kohei、Ebine Makoto、Satake Masayuki、Oishi Tohru
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 3 Pages: 265-268

    • DOI

      10.1246/cl.171056

    • NAID

      130006434032

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Syntheses and Biological Activities of the LMNO, ent-LMNO, and NOPQR(S) Ring Systems of Maitotoxin2017

    • Author(s)
      Onoue Hisaaki、Marubayashi Riho、Ishikawa Erina、Konoki Keiichi、Torikai Kohei、Ebine Makoto、Murata Michio、Oishi Tohru
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 18 Pages: 9595-9618

    • DOI

      10.1021/acs.joc.7b01658

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Design and synthesis of benzoacridines as estrogenic and anti-estrogenic agents2017

    • Author(s)
      Torikai Kohei、Koga Rintaro、Liu Xiaohui、Umehara Kaoru、Kitano Tatsuya、Watanabe Kenji、Oishi Tohru、Noguchi Hiroshi、Shimohigashi Yasuyuki
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 25 Issue: 20 Pages: 5216-5237

    • DOI

      10.1016/j.bmc.2017.07.067

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups: New members of the benzyl- and benzyloxymethyl-type family2017

    • Author(s)
      Sato, T.; Joh, Y.; Oishi, T.; Torikai, K.
    • Journal Title

      Tetrahedron Lett.

      Volume: 58 Issue: 23 Pages: 2178-2181

    • DOI

      10.1016/j.tetlet.2017.04.046

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tuned Classical Thermal Aromatization Furnishing an Estrogenic Benzoacridine2015

    • Author(s)
      Koga, R.; Oishi, T.; Torikai, K.
    • Journal Title

      Synlett

      Volume: 26 Issue: 20 Pages: 2801-2805

    • DOI

      10.1055/s-0035-1560521

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] 2-Naphthylmethoxymethyl as a Mildly Introducible and Oxidatively Removable Benzyloxymethyl-Type Protecting Group2015

    • Author(s)
      Sato, T.; Oishi, T.; Torikai, K.
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 12 Pages: 3110-3113

    • DOI

      10.1021/acs.orglett.5b01408

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Development of Novel Benzyloxymethyl Protecting Groups and Their Application to the Stereoselective Glycosylation2018

    • Author(s)
      Torikai, K.
    • Organizer
      255th ACS National Meeting 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ラセミ化の抑制を志向したπ-N保護ヒスチジンの合成2017

    • Author(s)
      Yanagimoto, R.
    • Organizer
      第29回若手研究者のためのセミナー(有機合成化学協会九州山口支部)
    • Related Report
      2017 Annual Research Report
  • [Presentation] ラセミ化の抑制を志向したπ-N保護ヒスチジンの合成2017

    • Author(s)
      Yanagimoto, R.
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 2-Naphthylmethoxymethyl: A mildly introducible and oxidatively removable benzyloxymethoxymethyl-type protecting group2016

    • Author(s)
      Torikai, K.
    • Organizer
      International Conference on Organic Chemistry
    • Place of Presentation
      Las Vegas, USA
    • Year and Date
      2016-08-10
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 2-Naphthylmethoxymethyl (NAPOM) Group -a New Member of the BOM Protective Group Family-2015

    • Author(s)
      Torikai, K.
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 2-Naphthylmethoxymethyl as a Mildly Introducible and Oxidatively Removable Benzyloxymethyl-Type Protecting Group2015

    • Author(s)
      Torikai, K.
    • Organizer
      IKCOC-13
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2015-11-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナフチルメトキシメチル:穏和な条件で導入・除去可能なヒドロキシ保護基2015

    • Author(s)
      鳥飼浩平
    • Organizer
      九州大学新技術説明会
    • Place of Presentation
      東京
    • Year and Date
      2015-10-16
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] ナフチルメトキシメチル:穏和な条件で導入・除去可能なヒドロキシ保護基2015

    • Author(s)
      鳥飼浩平
    • Organizer
      第18回生理活性をあまり意図しない自由な天然物合成勉強会
    • Place of Presentation
      大阪
    • Year and Date
      2015-10-03
    • Related Report
      2015 Research-status Report
  • [Remarks] 九州大学-研究者情報 [鳥飼浩平]

    • URL

      http://hyoka.ofc.kyushu-u.ac.jp/search/details/K003874/index.html

    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] アルコキシアルキル基を有する化合物およびそれを用いたアセタール系化合物の製造方法,ならびにその計測方法2017

    • Inventor(s)
      鳥飼 浩平
    • Industrial Property Rights Holder
      国立大学法人 九州大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] ヒドロキシ基及び/又はメルカプト基用保護基導入剤2017

    • Inventor(s)
      鳥飼浩平
    • Industrial Property Rights Holder
      九州大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-553062
    • Filing Date
      2017-02-13
    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] ヒドロキシ基及び/又はメルカプト基用保護基導入剤2015

    • Inventor(s)
      鳥飼浩平
    • Industrial Property Rights Holder
      国立大学法人九州大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2015-09-30
    • Related Report
      2015 Research-status Report
    • Overseas

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Published: 2015-04-16   Modified: 2019-03-29  

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