Synthesis of CH<sub>2</sub>-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct <i>C</i>-glycosylation
Yu Hidaka, Noriaki Kiya, Makoto Yoritate, Kazuteru Usui, Go Hirai
Abstract
Direct <italic>C</italic>-glycosylation of a conformationally constrained and stable C1-sp<sup>3</sup> hybridized carbohydrate donor with a carefully designed sphingosine unit afforded the CH<sub>2</sub>-linked analogue of antitumor-active KRN7000 and its glucose congener.
Topics & Concepts
ChemistryGlycosylationGlycosidic bondGlycosylGlycolipidGlycanStereochemistrySphingosineCongenerCarbohydrateBiochemistryCombinatorial chemistryOrganic chemistryGlycoproteinEnzymeReceptorCarbohydrate Chemistry and SynthesisImmune Cell Function and InteractionSphingolipid Metabolism and Signaling