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WO2008090829A1 - リボ核酸化合物の製造方法 - Google Patents

リボ核酸化合物の製造方法 Download PDF

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Publication number
WO2008090829A1
WO2008090829A1 PCT/JP2008/050670 JP2008050670W WO2008090829A1 WO 2008090829 A1 WO2008090829 A1 WO 2008090829A1 JP 2008050670 W JP2008050670 W JP 2008050670W WO 2008090829 A1 WO2008090829 A1 WO 2008090829A1
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WO
WIPO (PCT)
Prior art keywords
ribonucleic acid
acid compound
group
general formula
compound represented
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2008/050670
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English (en)
French (fr)
Inventor
Kohei Yamada
Hidetoshi Kitagawa
Kouichi Uetake
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Nippon Shinyaku Co Ltd
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Nippon Shinyaku Co Ltd
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Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd
Publication of WO2008090829A1 publication Critical patent/WO2008090829A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/167—Purine radicals with ribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

本発明の目的は、３’位の水酸基と５’位の水酸基がケイ素置換基で保護され、核酸塩基部のアミノ基又はヒドロキシ基が保護されていないリボ核酸化合物において、リボースの２’位の水酸基に、例えば、２－シアノエトキシメチル（ＣＥＭ）基を選択的かつ効率的に導入できるリボ核酸化合物の製造方法を提供することにある。 次の一般式（３）で表されるリボ核酸化合物を製造する方法において、ヨウ素と酸の存在下、次の一般式（１）で表されるリボ核酸化合物に次の一般式（２）で表されるモノチオアセタール化合物を反応させることによって、次の一般式（３）で表されるリボ核酸化合物を製造する。 式（１）、（２）及び（３）中、Ｂは保護基を有しない核酸塩基又はその修飾体を表し、ＷＧは電子吸引性基を表し、Ｒ１はアルキル又はアリールを表し、Ａはケイ素置換基を表す。
PCT/JP2008/050670 2007-01-22 2008-01-21 リボ核酸化合物の製造方法 Ceased WO2008090829A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-011813 2007-01-22
JP2007011813A JP2008174524A (ja) 2007-01-22 2007-01-22 リボ核酸化合物の製造方法

Publications (1)

Publication Number Publication Date
WO2008090829A1 true WO2008090829A1 (ja) 2008-07-31

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PCT/JP2008/050670 Ceased WO2008090829A1 (ja) 2007-01-22 2008-01-21 リボ核酸化合物の製造方法

Country Status (2)

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JP (1) JP2008174524A (ja)
WO (1) WO2008090829A1 (ja)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013027843A1 (ja) * 2011-08-25 2013-02-28 株式会社ボナック 配糖体化合物、チオエーテルの製造方法、エーテル、エーテルの製造方法、配糖体化合物の製造方法、核酸の製造方法
WO2018070543A1 (ja) 2016-10-14 2018-04-19 株式会社ボナック 新規な配糖体化合物及びその製造方法
US10377788B2 (en) 2015-04-02 2019-08-13 Bonac Corporation Method for producing glycoside compounds
US11401296B2 (en) 2018-04-24 2022-08-02 Sumitomo Chemical Company, Limited Amidite compound and method for producing polynucleotide using said compound
WO2023097308A1 (en) 2021-11-29 2023-06-01 Hongene Biotech Corporation Synthesis of 2' acetyl-ester protected nucleosides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010079813A1 (ja) * 2009-01-07 2010-07-15 日本新薬株式会社 イノシン誘導体の製造方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5695198A (en) * 1979-10-03 1981-08-01 Uni Baamingamu Za Ee55*22halogenovinyl**2**deoxycytidines
JPS5862195A (ja) * 1981-10-08 1983-04-13 Yamasa Shoyu Co Ltd １−β−Ｄ−アラビノフラノシル−（Ｅ）−５−（２−ハロゲノビニル）ウラシルの製造法
WO2003015798A1 (fr) * 2001-08-14 2003-02-27 Toyama Chemical Co., Ltd. Nouvelle methode virocide/inhibitrice de la proliferation virale et nouvel analogue de pyradine nucleotide/pyradine nucleoside
WO2005023828A1 (ja) * 2003-09-02 2005-03-17 Takeshi Wada リボヌクレオチド又はリボヌクレオチド誘導体の製造方法
WO2006022323A1 (ja) * 2004-08-26 2006-03-02 Nippon Shinyaku Co., Ltd. ホスホロアミダイト化合物及びオリゴｒｎａの製法
WO2006033730A2 (en) * 2004-08-20 2006-03-30 Dharmacon, Inc. Novel polynucleotide synthesis labeling chemistry
WO2007097447A1 (ja) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. 核酸保護基の脱離方法
WO2007097446A1 (ja) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. オリゴ核酸のキャッピング法
WO2007099896A1 (ja) * 2006-02-27 2007-09-07 Nippon Shinyaku Co., Ltd. 核酸保護基の脱離方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5695198A (en) * 1979-10-03 1981-08-01 Uni Baamingamu Za Ee55*22halogenovinyl**2**deoxycytidines
JPS5862195A (ja) * 1981-10-08 1983-04-13 Yamasa Shoyu Co Ltd １−β−Ｄ−アラビノフラノシル−（Ｅ）−５−（２−ハロゲノビニル）ウラシルの製造法
WO2003015798A1 (fr) * 2001-08-14 2003-02-27 Toyama Chemical Co., Ltd. Nouvelle methode virocide/inhibitrice de la proliferation virale et nouvel analogue de pyradine nucleotide/pyradine nucleoside
WO2005023828A1 (ja) * 2003-09-02 2005-03-17 Takeshi Wada リボヌクレオチド又はリボヌクレオチド誘導体の製造方法
WO2006033730A2 (en) * 2004-08-20 2006-03-30 Dharmacon, Inc. Novel polynucleotide synthesis labeling chemistry
WO2006022323A1 (ja) * 2004-08-26 2006-03-02 Nippon Shinyaku Co., Ltd. ホスホロアミダイト化合物及びオリゴｒｎａの製法
WO2007097447A1 (ja) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. 核酸保護基の脱離方法
WO2007097446A1 (ja) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. オリゴ核酸のキャッピング法
WO2007099896A1 (ja) * 2006-02-27 2007-09-07 Nippon Shinyaku Co., Ltd. 核酸保護基の脱離方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SHIBA Y. ET AL.: "Chemical synthesis of a very long oligoribonucleotide with 2-cyanoethoxymethyl (CEM9 as the 2'-O-protecting group: structural identification and biological activity of an synthetic 110mer precursor-microRNA candidate", NUCL. ACIDS RES., vol. 35, no. 10, pages 3287 - 3396 *
WADA T. ET AL.: "Regioselective protection of the 2'-hydroxyl group of N-acyl-3',5'-O-di(t-butyl)silanediylnucleoside derivatives by use if t-BuMgCl and 2-(trimethylsilyl)ethoxymethyl chloride", TETRAHEDRON LETT., vol. 36, no. 10, 1995, pages 1683 - 1684, XP004028564, DOI: doi:10.1016/0040-4039(95)00130-5 *

Cited By (16)

* Cited by examiner, † Cited by third party
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KR101761103B1 (ko) 2011-08-25 2017-07-25 가부시키가이샤 보낙 글리코시드 화합물, 티오에테르의 제조방법, 에테르, 에테르의 제조방법, 글리코시드 화합물의 제조방법, 핵산의 제조방법
AU2012297612B9 (en) * 2011-08-25 2017-08-03 Sumitomo Chemical Company, Limited Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside compound, method for producing nucleic acid
CN103906758A (zh) * 2011-08-25 2014-07-02 株式会社博纳克 配糖体化合物、硫醚的制造方法、醚、醚的制造方法、配糖体化合物的制造方法及核酸的制造方法
JP5554881B2 (ja) * 2011-08-25 2014-07-23 株式会社ボナック 配糖体化合物、チオエーテルの製造方法、エーテル、エーテルの製造方法、配糖体化合物の製造方法、核酸の製造方法
EP2749565A4 (en) * 2011-08-25 2015-08-05 Bonac Corp GLYCOSIDE COMPOUND, METHOD FOR THE PRODUCTION OF THIOETHERS, ETHER, METHOD FOR THE PRODUCTION OF, ETHER, METHOD FOR THE PRODUCTION OF A GLYCOSIDE COMPOUND, PROCESS FOR THE PREPARATION OF A NUCLEIC ACID
US9481702B2 (en) 2011-08-25 2016-11-01 Bonac Corporation Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid
AU2012297612A1 (en) * 2011-08-25 2014-03-20 Sumitomo Chemical Company, Limited Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside compound, method for producing nucleic acid
EP3098230A1 (en) * 2011-08-25 2016-11-30 Bonac Corporation Thioether compound for the protection of the 2'-hydroxy group in nucleosides to be used in oligonucleotide synthesis.
WO2013027843A1 (ja) * 2011-08-25 2013-02-28 株式会社ボナック 配糖体化合物、チオエーテルの製造方法、エーテル、エーテルの製造方法、配糖体化合物の製造方法、核酸の製造方法
CN103906758B (zh) * 2011-08-25 2017-05-10 株式会社博纳克 配糖体化合物、硫醚的制造方法、醚、醚的制造方法、配糖体化合物的制造方法及核酸的制造方法
US9988415B2 (en) 2011-08-25 2018-06-05 Bonac Corporation Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid
US10377788B2 (en) 2015-04-02 2019-08-13 Bonac Corporation Method for producing glycoside compounds
WO2018070543A1 (ja) 2016-10-14 2018-04-19 株式会社ボナック 新規な配糖体化合物及びその製造方法
US11401296B2 (en) 2018-04-24 2022-08-02 Sumitomo Chemical Company, Limited Amidite compound and method for producing polynucleotide using said compound
WO2023097308A1 (en) 2021-11-29 2023-06-01 Hongene Biotech Corporation Synthesis of 2' acetyl-ester protected nucleosides
US11897914B2 (en) 2021-11-29 2024-02-13 Hongene Biotech Corporation Synthesis of 2′ protected nucleosides

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