93612-84-1Relevant articles and documents
Two New Protected Acyl Protecting Groups for Alcoholic Hydroxy Functions
Brown, Jonathan M.,Christodoulou, Chris,Reese, Colin B.,Sindona, Giovanni
, p. 1785 - 1790 (2007/10/02)
4-(Methylthiomethoxy)butyric acid (13a) and 2-(methylthiomethoxymethyl)benzoic acid (14a) have been prepared in 53 and 64percent overall yields from γ-butyrolactone and phthalide, respectively.Thymidine reacts regioselectively with (13a) and (14a), in the presence of an appropriate condensing agent, to give the corresponding 5'-O-acyl derivatives , both in 70percent yield.The latter compounds undergo deacylation relatively slowly when treated with concentrated aqueous ammonia, but following treatment with mercury(II) perchlorate in the presence of 2,4,6-collidine in slightly wet tetrahydrofuran, are both converted back into thymidine under very mild conditions of basic hydrolysis.
