Synthesis of 8-heteroaryl-2'-deoxyguanosine derivatives

We describe the synthesis of 8-heteroaromatic-2'-deoxyguanosine analogues using Suzuki-Miyaura or Stille conditions. Unprotected and protected 8-bromo-2'-deoxyguanosine was coupled with commercially available heteroarylboronic acids or the trialkyltin derivatives of 2-pyridylbromides eithe...

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Bibliographic Details
Published inSynlett Vol. 2008; no. 10; pp. 1510 - 1514
Main Authors Hobley, Gerard, Gubala, Vladimir, Rivera-Sanchez, Maria Del C., Rivera, Jose M.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
CROSS-COUPLING REACTION
ANALOGS
G-QUARTETS
ADENOSINE
Stille reaction
coupling
nucleosides
LIGANDS
nucleobases
DNA
CHEMISTRY
palladium
2'-DEOXYGUANOSINE
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Summary:We describe the synthesis of 8-heteroaromatic-2'-deoxyguanosine analogues using Suzuki-Miyaura or Stille conditions. Unprotected and protected 8-bromo-2'-deoxyguanosine was coupled with commercially available heteroarylboronic acids or the trialkyltin derivatives of 2-pyridylbromides either with or without microwave irradiation in good yields.
Bibliography:Medline
NIH RePORTER
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-1077795