The Reaction of 2′-Deoxynucleosides with N-(2-Chloro-1,1,2-trifluoroethyl)diethylamine: Mechanisms of O2,3′-Anhydro-2′-deoxynucleoside and By-product Formation

Abstract

Reaction mechanisms consistent with the formation of isopropylidene-like trans-furanose-3′,5′-[2-(R)(S)-aminochlorofluoromethyl-1,3-dioxanyl]-2′-deoxynucleoside intermediates 6, O ² ,3′-anhydro-2′-deoxynucleosides 7 and other minor reaction products and the yield-limiting effect of 6 on the cyclization of 7 are proposed.