WO2008090829A1 - Process for production of ribonucleic acid compound - Google Patents

Process for production of ribonucleic acid compound 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
Authority
WO
WIPO (PCT)
Prior art keywords
ribonucleic acid
acid compound
group
general formula
compound represented
Prior art date
Application number
PCT/JP2008/050670
Other languages
French (fr)
Japanese (ja)
Inventor
Kohei Yamada
Hidetoshi Kitagawa
Kouichi Uetake
Original Assignee
Nippon Shinyaku Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Shinyaku Co., Ltd. filed Critical Nippon Shinyaku Co., Ltd.
Publication of WO2008090829A1 publication Critical patent/WO2008090829A1/en

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Classifications

    • 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

Landscapes

  • 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

Disclosed is a process for producing a ribonucleic acid compound in which each of hydroxyl groups at position-3' and position-5' is protected by a silicon substituent, an amino group or an hydroxy group in the nucleic acid base moiety is not protected, and a 2-cyanoethyxymethyl (CEM) group or the like can be introduced into a hydroxyl group at position-2' in the ribose moiety selectively and efficiently. Specifically disclosed is a ribonucleic acid compound represented by the general formula (3), which comprises the step of reacting a ribonucleic acid compound represented by the general formula (1) with a monothioacetal compound represented by the general formula (2) in the presence of iodine and an acid to produce the ribonucleic acid compound represented by the general formula (3). In the formulae (1), (2) and (3), B represents a nucleic acid base having no protecting group or a modified form thereof; WG represents an electron-withdrawing group; R1 represents an alkyl or an aryl; and A represents a silicon substituent.
PCT/JP2008/050670 2007-01-22 2008-01-21 Process for production of ribonucleic acid compound WO2008090829A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007011813A JP2008174524A (en) 2007-01-22 2007-01-22 Manufacturing method of ribonucleic acid compound
JP2007-011813 2007-01-22

Publications (1)

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

Family

ID=39644406

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/050670 WO2008090829A1 (en) 2007-01-22 2008-01-21 Process for production of ribonucleic acid compound

Country Status (2)

Country Link
JP (1) JP2008174524A (en)
WO (1) WO2008090829A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013027843A1 (en) * 2011-08-25 2013-02-28 株式会社ボナック Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside compound, method for producing nucleic acid
WO2018070543A1 (en) 2016-10-14 2018-04-19 株式会社ボナック Novel glycoside compound and production method therefor
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 (en) * 2009-01-07 2010-07-15 日本新薬株式会社 Method for manufacturing inosine derivative

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 (en) * 1981-10-08 1983-04-13 Yamasa Shoyu Co Ltd Production of 1-beta-d-arabinofuranosyl-(e)-5-(2- halogenovinyl)uracil
WO2003015798A1 (en) * 2001-08-14 2003-02-27 Toyama Chemical Co., Ltd. Novel virus proliferation inhibition/virucidal method and novel pyradine nucleotide/pyradine nucleoside analogue
WO2005023828A1 (en) * 2003-09-02 2005-03-17 Takeshi Wada Process for producing ribonucleotide or ribonucleotide derivative
WO2006022323A1 (en) * 2004-08-26 2006-03-02 Nippon Shinyaku Co., Ltd. Phosphoramidite compound and method for producing oligo-rna
WO2006033730A2 (en) * 2004-08-20 2006-03-30 Dharmacon, Inc. Novel polynucleotide synthesis labeling chemistry
WO2007097446A1 (en) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. Method of capping oligonucleic acid
WO2007097447A1 (en) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. Method for removal of nucleic acid-protecting group
WO2007099896A1 (en) * 2006-02-27 2007-09-07 Nippon Shinyaku Co., Ltd. Method for detaching protecting group on nucleic acid

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 (en) * 1981-10-08 1983-04-13 Yamasa Shoyu Co Ltd Production of 1-beta-d-arabinofuranosyl-(e)-5-(2- halogenovinyl)uracil
WO2003015798A1 (en) * 2001-08-14 2003-02-27 Toyama Chemical Co., Ltd. Novel virus proliferation inhibition/virucidal method and novel pyradine nucleotide/pyradine nucleoside analogue
WO2005023828A1 (en) * 2003-09-02 2005-03-17 Takeshi Wada Process for producing ribonucleotide or ribonucleotide derivative
WO2006033730A2 (en) * 2004-08-20 2006-03-30 Dharmacon, Inc. Novel polynucleotide synthesis labeling chemistry
WO2006022323A1 (en) * 2004-08-26 2006-03-02 Nippon Shinyaku Co., Ltd. Phosphoramidite compound and method for producing oligo-rna
WO2007097446A1 (en) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. Method of capping oligonucleic acid
WO2007097447A1 (en) * 2006-02-27 2007-08-30 Nippon Shinyaku Co., Ltd. Method for removal of nucleic acid-protecting group
WO2007099896A1 (en) * 2006-02-27 2007-09-07 Nippon Shinyaku Co., Ltd. Method for detaching protecting group on nucleic acid

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 (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103906758B (en) * 2011-08-25 2017-05-10 株式会社博纳克 Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside compound, method for producing nucleic acid
EP2749565A4 (en) * 2011-08-25 2015-08-05 Bonac Corp Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid
WO2013027843A1 (en) * 2011-08-25 2013-02-28 株式会社ボナック Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside compound, method for producing nucleic acid
JP5554881B2 (en) * 2011-08-25 2014-07-23 株式会社ボナック Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid
KR101761103B1 (en) 2011-08-25 2017-07-25 가부시키가이샤 보낙 Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing 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
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.
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 (en) * 2011-08-25 2014-07-02 株式会社博纳克 Glucoside compound, method for producing thioether, ether, method for producing ether, method for producing glucoside 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
AU2012297612B2 (en) * 2011-08-25 2017-02-23 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
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 (en) 2016-10-14 2018-04-19 株式会社ボナック Novel glycoside compound and production method therefor
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

Also Published As

Publication number Publication date
JP2008174524A (en) 2008-07-31

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