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Total syntheses and reaction developments on the basis of axial-rich sugars

Research Project

Project/Area Number 22550047
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKwansei Gakuin University

Principal Investigator

YAMADA Hidetoshi  関西学院大学, 理工学部, 教授 (90200732)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2012: ¥260,000 (Direct Cost: ¥200,000、Indirect Cost: ¥60,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords合成有機化学 / 天然物合成 / アキシアル・リッチ糖 / エラジタンニン / 化学合成 / 3、6位架橋糖 / グリコシル化反応 / 立体選択的 / 有機化学 / 糖質 / ポリフェノール
Research Abstract

Utilizing the unique property of sugar derivatives, which conformation were locked into the axial-rich conformation, we developed (1) synthesis of ellagitannins and (2) stereoselective glycosylation reactions. In the research for (1), new synthetic routes for the axial-rich ellagitannins were developed to increase the lead in the aria of ellagitannin synthesis. For (2), highly α-selective glycosylations were developed by applying the sugars locked to the axial-rich conformations.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (60 results)

All 2013 2012 2011 2010 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (44 results) (of which Invited: 1 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Roxbin B is Cuspinin; Structural Revision and Total Synthesis2013

    • Author(s)
      Yamaguchi, S.; Hirokane, T.; Yoshida, T.; Tanaka, T.; Hatano, T.; Ito, H.; Nonaka, G.; Ya mada, H.
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 11 Pages: 5410-5417

    • DOI

      10.1021/jo400562k

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] High Yield Total Synthesis of (-)-Strictinin through Intramolecular Coupling of Gallates2013

    • Author(s)
      Michihata, N.; Kaneko, Y.; Kasai, Y.; Tanigawa, K.;Hirokane, T.; Higasa, S.; Ya mada, H.
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 9 Pages: 4319-4328

    • DOI

      10.1021/jo4003135

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of the Proposed Structure of Roxbin B; the Nonidentical Outcome2012

    • Author(s)
      Yamaguchi, S.; Ashikaga, Y.; Nishii, K.; Ya mada, H.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 23 Pages: 5928-5931

    • DOI

      10.1021/ol302845n

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-Davidiin, Kasai2012

    • Author(s)
      Y.; Michihata, N.; Nishimura. H.; Hirokane, T.; Ya mada, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 10 Pages: 8026-8029

    • DOI

      10.1055/s-0032-1317276

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Completely β-Selective Glycosylation Using3,6-O-(O-Xylylene)-Bridged Axial-Rich Glucosyl Fluoride.2012

    • Author(s)
      Okada, Y.; Asakura, N.; Bando, M.; Ashikaga, Y.; Ya mada, H.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 16 Pages: 6940-6943

    • DOI

      10.1021/ja301480g

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Strategies and Methods for the Total Synthesis of Ellagitannins.2012

    • Author(s)
      Ya mada, H.; Hirokane, T.; Asakura, N.; Kasai, Y.; Nagao, K.
    • Journal Title

      Curr. Org. Chem.

      Volume: 16 Issue: 5 Pages: 578-604

    • DOI

      10.2174/138527212799859426

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-Davidiin2012

    • Author(s)
      Hidetoshi, Yamada, Yusuke Kasai
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 32 Pages: 8026-8029

    • DOI

      10.1002/anie.201203305

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds.2011

    • Author(s)
      Asakura, N.; Fujimoto, S.; Michihata, N.; Nishii, K.; Imagawa, H.; Ya mada, H.
    • Journal Title

      J. Org. Chem.

      Volume: 76 Issue: 23 Pages: 9711-9719

    • DOI

      10.1021/jo201750d

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] O-Glycosylation Reaction Using Axial-rich Glycosyl Donors2011

    • Author(s)
      Ya mada, H.
    • Journal Title

      Trends in Glycoscience and Glycotechnology

      Volume: 23 Issue: 131 Pages: 122-133

    • DOI

      10.4052/tigg.23.122

    • NAID

      10029582877

    • ISSN
      0915-7352, 1883-2113
    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Sieves 5A as an Acidic Reagent: the Discovery and Applications.2011

    • Author(s)
      Asakura, N.; Hirokane, T.; Hoshida, H.; Ya mada, H.
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Issue: 4 Pages: 534-537

    • DOI

      10.1016/j.tetlet.2010.11.113

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Molecular sieves 5A as an acidic reagent : the discovery and applications2011

    • Author(s)
      N.Asakura
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 534-537

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Strategies and Methods for the Total Synthesis of Ellagitannins2011

    • Author(s)
      H.Yamada
    • Journal Title

      Curr.Org.Chem

      Volume: 14(In press)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 3,6-O-[ビベンジル-2,2'-ビス(メチレン)]架橋糖を用いた高α選択的グルコシル化反応2013

    • Author(s)
      平田恭章・足利是貴・山田英俊
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Year and Date
      2013-03-23
    • Related Report
      2012 Final Research Report
  • [Presentation] ss-ペンタガロイルグルコース誘導体のアリールカップリングによる3,6-HHDP架橋体の単離2013

    • Author(s)
      久米裕二・芦辺成矢・上野友理・岩下孝・山田英俊
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Year and Date
      2013-03-23
    • Related Report
      2012 Final Research Report
  • [Presentation] 3,6-O-(o-キシリレン)架橋によりアキシアル・リッチな立体配座としたフッ化糖を用いるβ-グリコシル化反応2012

    • Author(s)
      山田英俊
    • Organizer
      第10回糖鎖科学コンソーシアムシンポジウム
    • Place of Presentation
      東京コンファレンスセンター(品川)
    • Year and Date
      2012-11-30
    • Related Report
      2012 Final Research Report
  • [Presentation] Total Synthesis of anAxial-Rich Ellagitannin, Corilagin2012

    • Author(s)
      Yamada, H.
    • Organizer
      13thInternational Symposium on NaturalProduct Chemistry
    • Place of Presentation
      University of Karachi, Pakistan,oral,Invited speaker
    • Year and Date
      2012-09-23
    • Related Report
      2012 Final Research Report
  • [Presentation] ラゲルスタンニンCの全合成とロキシビン Bの構造訂正・全合成2012

    • Author(s)
      山口左有里、金子由季、広兼司、足利是貴、西井健太郎、道畑直起、山田英俊
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京農業大学世田谷キャンパス
    • Year and Date
      2012-09-20
    • Related Report
      2012 Final Research Report
  • [Presentation] Totalsynthesis of praecoxin B2012

    • Author(s)
      Hirokane, T.; Naoki, M.; Asakura, N.; Mitamura, T.; Yamada, H
    • Organizer
      26thInternational Conference on Polyphenols
    • Place of Presentation
      Firenche, Italy,poster,Awarded a poster prize
    • Year and Date
      2012-07-23
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds2012

    • Author(s)
      Asakura, N.; Fujimoto, S.; Michihata, N.; Nishii, K.; Imagawa, H.; Yamada, H
    • Place of Presentation
      Firenche, Italy
    • Year and Date
      2012-07-23
    • Related Report
      2012 Final Research Report
  • [Presentation] 軸不斉HexaHydroxyDiPhenoyl基の使いかた2012

    • Author(s)
      山田英俊
    • Organizer
      第2回有機分子構築法夏の勉強会
    • Place of Presentation
      ラフォーレ蔵王リゾート&スパ
    • Year and Date
      2012-05-19
    • Related Report
      2012 Final Research Report
  • [Presentation] 2,4-O(-2,2'-ビベンジルビス(メチレン)架橋を用いた2012

    • Author(s)
      足利是貴・廣兼司・山田英俊
    • Organizer
      D-グルコースの環立体配座制御
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] Roxbin Bの全合成研究2012

    • Author(s)
      山口左有里
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] 2,4-O(-2,2'-ビベンジルビス(メチレン)架橋を用いたD-グルコースの環立体配座制御2012

    • Author(s)
      足利是貴
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] RoxbinBの全合成研究2012

    • Author(s)
      山口左有里・足利是貴・山田英俊
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] ss-ペンタガロイルグルコース誘導体のヘキサヒドロキシジフェノイル架橋2011

    • Author(s)
      芦辺成矢,藤本翔平,上野友理,広兼司,久米裕二,山田英俊
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      2011-09-30
    • Related Report
      2012 Final Research Report
  • [Presentation] β-ペンタガロイルグルコース誘導体のヘキサヒドロキシジフェノイル架橋2011

    • Author(s)
      芦辺成矢
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      2011-09-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] Molecular sieves 5A as an acidic reagent : the discovery and applications2011

    • Author(s)
      Asakura, N.
    • Organizer
      XXII French-Japanese Symposium on Medecinal and Fine Chemistry
    • Place of Presentation
      Rouen, France
    • Year and Date
      2011-09-11
    • Related Report
      2011 Annual Research Report
  • [Presentation] Formation of C-O bond in valoneoyl group and synthetic study of Calamanin A2011

    • Author(s)
      Hirokane, T.
    • Organizer
      第46回天然物化学談話会
    • Place of Presentation
      熱川ハイツ(静岡)
    • Year and Date
      2011-07-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Roxbin Bの全合成研究2011

    • Author(s)
      山口左有里
    • Organizer
      第46回天然物化学談話会
    • Place of Presentation
      熱川ハイツ(静岡)
    • Year and Date
      2011-07-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Lagerstannin Cの全合成2011

    • Author(s)
      金子由季
    • Organizer
      第46回天然物化学談話会
    • Place of Presentation
      熱川ハイツ(静岡)
    • Year and Date
      2011-07-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] モレキュラーシーブス5Aの酸触媒としての利用2011

    • Author(s)
      広兼司
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] 3,6-O-(o-キシリレン)架橋糖を用いた高.alpha.立体選択的グルコシル化反応2011

    • Author(s)
      本山敦之
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ヘキサヒドロキシジフェノイル化合物のフロー合成2011

    • Author(s)
      丹田健太郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] D-グルコン酸部分を持つエラジタンニン、ラゲルスタンニンCの合成研究2011

    • Author(s)
      金子由季
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] D-グルコン酸部分を持つエラジタンニン、ラゲルスタンニンCの合成研究2011

    • Author(s)
      金子由季・丹田健太郎・道畑直起・山田英俊
    • Organizer
      日本化学会第91春季年会
    • Year and Date
      2011-03-11
    • Related Report
      2012 Final Research Report
  • [Presentation] 3,6-O-(o-キシリレン)架橋糖を用いた高立体選択的グルコシル化反応2011

    • Author(s)
      本山敦之・足利是貴・山田英俊
    • Organizer
      日本化学会第91春季年会
    • Year and Date
      2011-03-11
    • Related Report
      2012 Final Research Report
  • [Presentation] 反転した糖を含むエラシ〓タンニンの全合成2010

    • Author(s)
      山田英俊
    • Organizer
      徳島文理大学薬学部戦略的基盤形成支援事業報告会
    • Place of Presentation
      徳島文理大学薬学部
    • Year and Date
      2010-12-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] Total synthesis of(-)-strictinin in high overall yield2010

    • Author(s)
      Naoki Michihata, Noriaki Asakura, Hidetoshi Yamada
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      HonoluluHawaii
    • Year and Date
      2010-12-16
    • Related Report
      2012 Final Research Report
  • [Presentation] Total Synthesis of (-)-Strictinin in High Overall Yield2010

    • Author(s)
      Michihata, Naoki
    • Organizer
      International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] アキシアル・リッチ糖を用いたβ-グルコシドの製造2010

    • Author(s)
      山田英俊
    • Organizer
      新技術説明会
    • Place of Presentation
      JSTホール(東京)
    • Year and Date
      2010-11-19
    • Related Report
      2012 Final Research Report
  • [Presentation] 鎖状ジテルペン配糖体Attenosideの全合成研究2010

    • Author(s)
      岸聖也
    • Organizer
      第54回TEAC
    • Place of Presentation
      山梨大学甲府キャンパス
    • Year and Date
      2010-10-23
    • Related Report
      2010 Annual Research Report
  • [Presentation] (+)-PraecoxinB,(-)-Strictininの全合成2010

    • Author(s)
      廣兼司,道畑直起,朝倉典昭,葛西祐介,谷川康太郎,三田村隆史,山田英俊
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      グランシップ静岡
    • Year and Date
      2010-09-29
    • Related Report
      2012 Final Research Report
  • [Presentation] (+)-Praecoxin B,(-)-Strictininの全合成2010

    • Author(s)
      廣兼司
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      グランシップ(静岡県コンベンションアーツセンター)
    • Year and Date
      2010-09-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis of 1,2,4-Orthoacetyl-_-D-Glucopyranose Utilizing Molecular Sieves2010

    • Author(s)
      N. Asakura, H. Hoshida, H. Yamada
    • Organizer
      The 25th lnternational Carbohydrate Symposium
    • Place of Presentation
      幕張メッセ
    • Year and Date
      2010-08-03
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of 1,2,4-Orthoacetyl-α-D-Glucopyranose Utilizing Molecular Sieves2010

    • Author(s)
      N.Asakura
    • Organizer
      The 25th International Carbohydrate Symposium (ICS2010)
    • Place of Presentation
      幕張メッセ国際会議場
    • Year and Date
      2010-08-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] 6-ヘキサヒドロキシジフェノイル架橋エラジタンニン、(+)-Davidiinの5段階合成2010

    • Author(s)
      芦辺成矢・朝倉典昭・藤本翔平・山田英俊,1
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2010-08-02
    • Related Report
      2012 Final Research Report
  • [Presentation] 1,6-ヘキサヒドロキシジフェノイル架橋エラジタンニン,(+)-ダビジインの5段階合成2010

    • Author(s)
      芦辺成矢
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] ジテルペン配糖体Attenodieの合成研究2010

    • Author(s)
      岸聖也
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] ヘキサヒドロキシジフェノイル化合物のフロー合成2010

    • Author(s)
      丹田健太郎
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] (-)-コリラジン全合成の単段階化とモレキュラーシーブ5Aの酸性反応剤としての利用2010

    • Author(s)
      山田英俊
    • Organizer
      第一回有機分子構築法夏の勉強会
    • Place of Presentation
      ラフォーレ蔵王リゾート&スパ
    • Year and Date
      2010-05-23
    • Related Report
      2012 Final Research Report
  • [Presentation] ラゲルスタンニンCの全合成とロキシビン Bの構造訂正・全合成

    • Author(s)
      山口左有里
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京農業大学世田谷キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 3, 6-O-(o-キシリレン)架橋によりアキシアル・リッチな立体配座としたフッ化糖を用いるβ-グリコシル化反応

    • Author(s)
      山田英俊
    • Organizer
      第10回糖鎖科学コンソーシアムシンポジウム
    • Place of Presentation
      東京コンファレンスセンター(品川)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] β-ペンタガロイルグルコース誘導体のアリールカップリングによる 3,6-HHDP架橋体の単離

    • Author(s)
      久米裕二
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 1,3-HHDP 架橋エラジタンニン , (+)-Hipporhamnin の合成研究

    • Author(s)
      山口左有里
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] フロー合成によるヘキサヒドロキシ ジフェノイル基合成法

    • Author(s)
      黒田和宏
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 3,6-O- [ビベンジル-2,2'-ビス(メチレン)]架橋 糖を用いた高α選択的グルコシル化反応

    • Author(s)
      平田恭章
    • Organizer
      第93回日本化学会年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 3,6-O-架橋反転ピラノース化合物及び α-O-ピラノシドの製造方法2013

    • Inventor(s)
      山田英俊
    • Industrial Property Rights Holder
      学校法人関西学院
    • Industrial Property Number
      2013-028518
    • Filing Date
      2013-02-18
    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 3,6-O-架橋反転ピラノース化合物及びss-O-ピラノシドの製造方法2013

    • Inventor(s)
      山田英俊、朝倉典昭、岡田康則
    • Industrial Property Rights Holder
      学校法人関西学院
    • Acquisition Date
      2013-05-02
    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 3,6-O-架橋反転ピラノース化合物及びα-O-ピラノシドの製造方法2013

    • Inventor(s)
      山田英俊
    • Industrial Property Rights Holder
      関西学院大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-028518
    • Filing Date
      2013-02-18
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 2,4-O-架橋反転ピラノース化合物2012

    • Inventor(s)
      山田英俊
    • Industrial Property Rights Holder
      学校法人関西学院
    • Industrial Property Number
      2012-032663
    • Filing Date
      2012-02-17
    • Related Report
      2012 Final Research Report 2011 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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