title: A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues.
abstract: A general and efficient approach was developed for the introduction of S-functionality at the C-5 position of cytosine and uracil nucleosides and their analogues. The key step is a palladium-catalyzed C-S coupling of the corresponding 5-bromo nucleoside derivative and alkyl thiol. The butyl 3-mercaptopropionate coupling products were further converted to the corresponding disulphides, the stable precursors of 5-mercaptopyrimidine nucleosides.
authors: Tallinn University of Technology, Department of Chemistry, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors: Dzmitry G
authors: DG
authors: Kananovich
authors: Alli
authors: A
authors: Reino
authors: Kaja
authors: K
authors: Ilmarinen
authors: Marko
authors: M
authors: Rõõmusoks
authors: Mati
authors: M
authors: Karelson
authors: Margus
authors: M
authors: Lopp
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D003596:Cytosine / Q000138:chemical synthesis / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry; D019259:Lamivudine / Q000031:analogs & derivatives / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013889:Thiouracil / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D004220:Disulfides; D011741:Pyrimidine Nucleosides; D019259:Lamivudine; D013889:Thiouracil; D003596:Cytosine