摘要
The protected ceramide: N-((2S,3S,4R)-3,4-bis(benzyloxy)-1-hydroxyoctadecan-2-yl)tetracosanamide, was attempted to introduce a triflate as a leaving group followed by a nucleophilic substitution with azido group in one-pot manner. Unexpectedly, the oxazole ring formed via a thermodynamically favored intramolecular cyclization was opened to generate the original ceramide by triflic acid. In addition, the residual acid promoted a formylation of the primary hydroxy group in DMF.