The behaviour of deoxyhexose trihaloacetimidates in selected glycosylations

Armed deoxyhexose glycosyl donors are very reactive and sometimes too uncontrollably activated in glycosylation reactions; yields can be thereby reduced, especially when unreactive glycosyl acceptors are involved. In this paper, the behaviour of a range of deoxyhexose trihaloacetimidate (trichloro- and N-phenyl trifluoro-) donors is compared in some selected glycosylations towards biologically relevant targets. The selected N-phenyl trifluoroacetimidates often afforded best results in terms of both donor synthesis and glycosylation yield.