ABSTRACT
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 alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.
Subject(s)
Allyl Compounds/chemistry , Glycosides/chemical synthesis , Antigens, Neoplasm/chemistry , Glucose/chemistry , Glycosides/chemistry , Glycosylation , Molecular Structure , StereoisomerismABSTRACT
[reaction: see text] The synthesis of stable, C-linked analogues of glycopeptides is being investigated with two complementary synthetic strategies, co-translational and post-translational glycopeptide synthesis. The key feature of the present approach lies in an effective olefin cross-metathesis reaction that allows formation of both glycoamino acids and glycopeptides.
