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Studies on the Stereoselective Synthesis of C-Allyl Glycosides

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journal contribution
posted on 2008-11-06, 00:00 authored by Glenn J. McGarvey, Christopher A. LeClair, Bahar A. Schmidtmann
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.