Abstract
Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α‐glucoside selectively. Use of less reactive acceptors led to the formation of α/β‐mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β‐glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2‐azido‐2‐deoxy‐glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α‐linked products in high yield in most cases.
Acknowledgment
This work was supported by an EU Marie Curie Intra‐European Fellowship (to R. v W) and by the Weston Foundation. We thank the UK EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.