Thiation of 2'-deoxy-5,6-dihydropyrimidine nucleosides with Lawesson's reagent: characterisation of oxathiaphosphepane intermediates.
Treatment of 2'-deoxy-3',5'-dithexyldimethylsilyl-5,6-dihydrouridine with Lawesson's reagent led to the expected C4-thiolated derivative together with a number of oxathiaphosphepane isomers which resulted from the heat reversible incorporation of an AnPS2 unit within the 2'-deoxyribose moiety explaining the subsequent anomerisation of the 5,6-dihydropyrimidine nucleosides.
Peyrane
Frédéric
F
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
Fourrey
Jean-Louis
JL
Clivio
Pascale
P
D003855:Deoxyribose / Q000737:chemistry; D006358:Hot Temperature; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D013237:Stereoisomerism; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry*
D009946:Organothiophosphorus Compounds; D011741:Pyrimidine Nucleosides; D013891:Thiouridine; D003855:Deoxyribose; C010922:5,6-dihydrouridine; C029887:2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide; D014529:Uridine