Sulfanyl radical promoted C4'-C5' bond scission of 5'-oxo-3',4'-didehydro-2',3'-dideoxynucleosides.
Treatment of C5'-aldehydes, under mildly basic conditions leads to the formation of 3',4'-didehydroaldehydes, and furfural. Sulfanyl radical addition eventually gives rise to the lactones, through C4'-C5' bond scission of the 1,2-dioxetane intermediates.
Navacchia
Maria Luisa
ML
ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy.
Montevecchi
Pier Carlo
PC
D015224:Dideoxynucleosides / Q000737:chemistry*; D005609:Free Radicals; D012997:Solvents; D013696:Temperature; D013997:Time Factors
D015224:Dideoxynucleosides; D005609:Free Radicals; D012997:Solvents