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 alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.
McGarvey
Glenn J
GJ
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, USA. gjm@virginia.edu
LeClair
Christopher A
CA
Schmidtmann
Bahar A
BA
D000498:Allyl Compounds / Q000737:chemistry*; D000951:Antigens, Neoplasm / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000498:Allyl Compounds; D000951:Antigens, Neoplasm; D006027:Glycosides; D005947:Glucose