Iodine Promoted Glycosylation with Glycosyl Iodides: a-Glycoside Synthesis 

 -  Journal of Carbohydrate Chemistry, 24, p.463-474, 2005 .
<br/><br/> Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave a-glucoside selectively. Use of less reactive acceptors led to the formation of a/b-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded b-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 a-linked products in high yield in most cases. 
<br/><br/><label>Subjects--Topical Terms: </label><br/>GLYCOSYL IODINE<br/>IODINE<br/>GLYCOSYLATED AMINO ACIDS<br/>A-GLYCOSYLATION