New dinucleoside analogues via cross-coupling metathesis.
Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.
Roy
Vincent
V
Laboratoire de Chimie des Substances Naturelles, Faculté des Sciences et Techniques, Université de Limoges, 123, Ave. Albert Thomas, Limoges 87060, France.
Zerrouki
Rachida
R
Krausz
Pierre
P
D002384:Catalysis; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D013936:Thymidine / Q000737:chemistry
D009696:Nucleic Acids; D009705:Nucleosides; D013936:Thymidine