P. Montevecchi, A. Manetto, Maria Luisa Navacchia
May 3, 2004
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron
Abstract
Abstract Thermal decomposition of the tert -butyl perester of thymidine-5′-carboxylic acid 1 carried out at 85 °C in different solvents affords the tert -butylacetal 4a , deriving from in cage decomposition, and pseudo C4′ radicals 2 . Radicals 2 can be reduced to 5 by hydrogen atom abstraction from thiol (thiophenol or glutathione) or THF, or can be oxidized to cations 8 by dioxygen or perester 1 itself. Cations 8 are stereoselectively trapped by the nucleophilic solvent ( tert -butanol, methanol, water) to give acetals 4a - c .