PL403256A1 - Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function - Google Patents

Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function

Info

Publication number
PL403256A1
PL403256A1 PL403256A PL40325613A PL403256A1 PL 403256 A1 PL403256 A1 PL 403256A1 PL 403256 A PL403256 A PL 403256A PL 40325613 A PL40325613 A PL 40325613A PL 403256 A1 PL403256 A1 PL 403256A1
Authority
PL
Poland
Prior art keywords
acetal
hydroxyl function
introduction
protect
protecting group
Prior art date
Application number
PL403256A
Other languages
Polish (pl)
Other versions
PL221806B1 (en
Inventor
Wojciech T. Markiewicz
Agnieszka Toś-Marciniak
Marcin Krzysztof Chmielewski
Original Assignee
Instytut Chemii Bioorganicznej Polskiej Akademii Nauk
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 Instytut Chemii Bioorganicznej Polskiej Akademii Nauk filed Critical Instytut Chemii Bioorganicznej Polskiej Akademii Nauk
Priority to PL403256A priority Critical patent/PL221806B1/en
Priority to PCT/PL2014/050012 priority patent/WO2014148928A1/en
Priority to EP14723139.3A priority patent/EP3016964A1/en
Publication of PL403256A1 publication Critical patent/PL403256A1/en
Publication of PL221806B1 publication Critical patent/PL221806B1/en

Links

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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Przedmiotem wynalazku jest sposób wprowadzania acetalowych i acetaloestrowych grup ochronnych funkcji hydroksylowej. Sposób ten znajduje zastosowanie w szczególności w procesach syntezy RNA. Sposób polega na reakcji związku organicznego zawierającego co najmniej jedną grupę hydroksylową, rozpuszczalnego w rozpuszczalniku aprotycznym, ze związkiem o wzorze ogólnym: R1-S-CH2-O-R2 w obecności SnCl4, w rozpuszczalniku aprotycznym. W drugim aspekcie przedmiotem wynalazku jest sposób ochrony funkcji hydroksylowej w szczególności w pozycji 2' pochodnych nukleozydowych polegający na wprowadzaniu grupy acetalowej lub acetaloestrowej.The subject of the invention is a method of introducing acetal and acetalester protecting groups of the hydroxyl function. This method finds application in particular in RNA synthesis processes. The method consists in the reaction of an organic compound containing at least one hydroxyl group, soluble in an aprotic solvent, with a compound of the general formula: R1-S-CH2-O-R2 in the presence of SnCl4, in an aprotic solvent. In a second aspect, the invention relates to a method of protecting the hydroxyl function in particular in the 2' position of nucleoside derivatives by introducing an acetal or acetal ester group.

PL403256A 2013-03-21 2013-03-21 Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function PL221806B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PL403256A PL221806B1 (en) 2013-03-21 2013-03-21 Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function
PCT/PL2014/050012 WO2014148928A1 (en) 2013-03-21 2014-03-19 Method for incorporating protecting acetal and acetal ester groups, and its application for the protection of hydroxyl function
EP14723139.3A EP3016964A1 (en) 2013-03-21 2014-03-19 Method for incorporating protecting acetal and acetal ester groups, and its application for the protection of hydroxyl function

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL403256A PL221806B1 (en) 2013-03-21 2013-03-21 Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function

Publications (2)

Publication Number Publication Date
PL403256A1 true PL403256A1 (en) 2014-05-26
PL221806B1 PL221806B1 (en) 2016-05-31

Family

ID=50687597

Family Applications (1)

Application Number Title Priority Date Filing Date
PL403256A PL221806B1 (en) 2013-03-21 2013-03-21 Method for introduction of acetal and acetal-ester protecting group and its use to protect a hydroxyl function

Country Status (3)

Country Link
EP (1) EP3016964A1 (en)
PL (1) PL221806B1 (en)
WO (1) WO2014148928A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4441066A1 (en) 2021-11-29 2024-10-09 Hongene Biotech Corporation Synthesis of 2' acetyl-ester protected nucleosides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1193598A (en) * 1982-05-06 1985-09-17 Rafael Foguet 2-amino-benzoic acid derivatives and processes for their production
US5986084A (en) 1997-08-18 1999-11-16 Pitsch; Stefan Ribonucleoside-derivative and method for preparing the same
US6458780B1 (en) * 1998-07-27 2002-10-01 Meiji Seika Kaisha, Ltd. Carbapenem derivatives
FR2931824B1 (en) 2008-05-29 2014-11-28 Centre Nat Rech Scient PROCESS FOR RNA SYNTHESIS THROUGH CHEMICAL.

Also Published As

Publication number Publication date
PL221806B1 (en) 2016-05-31
EP3016964A1 (en) 2016-05-11
WO2014148928A1 (en) 2014-09-25

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