Synthesis of the trisaccharide portion of the immunologic adjuvant QS-21A via sulfonium-mediated oxidative and dehydrative glycosylation.
[see structure]. The first synthesis of the trisaccharide fragment of the potent immunologic adjuvant QS-21A is reported. The key steps involve the application of sulfonium-mediated oxidative and dehydrative glycosidic couplings to construct the anomeric linkages in a short and convergent assembly of the branched trisaccharide.
Kim
Y J
YJ
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
Gin
D Y
DY
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry; D013452:Sulfonium Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000276:Adjuvants, Immunologic; D009844:Oligosaccharides; D012503:Saponins; D013452:Sulfonium Compounds; D014867:Water; C078785:saponin QA-21V1