Studies on the Stereoselective Synthesis of C-Allyl Glycosides

An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford α-allylation products in good to excellent yields, the search for conditions favoring β-selectivity proved less successful.