Glycosylations via in situ formation of glycosyl iodides from glycosyl bromides

Abstract

Glycosyl iodides have proven to be highly efficient and stereospecific glycosyl donors. Unfortunately with such high reactivity, they possess short shelf lives. Glycosyl bromides, on the other hand, are more robust than their iodo-counterparts. But, glycosylations using glycosyl bromides in the absence of Lewis acid catalysts are slow. Recently, we have demonstrated conditions augmenting glycosylations involving glycosyl bromides to levels matching the efficiency and stereospecificity of glycosyl iodides. Results of our studies will be discussed.