Nucleosides and nucleotides. 124. Chemical reactivity of the sugar moiety of 2'-deoxy-2'-methylidene pyrimidine nucleosides: Synthesis of 3'-amino-2',3'-dideoxy-2'-methylidene pyrimidine nucleosides via [2,3]-sigmatropic rearrangement of allylic selenides

Article abstract of DOI:10.1016/S0040-4020(01)80786-9

Nucleophilic substitution reactions of an allyl alcohol system in the 2'-deoxy-2'-methylidene pyrimidine nucleosides with various nucleophiles were investigated. The allyl alcohol system reacted with softer nucleophiles such as azide, thiophenoxide, and i