title: Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.
abstract: C-Glycoside analogues of α-galactosylceramide were synthesized in which several significant modifications known to promote Th-1 cytokine production were included. The key transformations include C-H oxidation, Sharpless asymmetric epoxidation, olefin cross metathesis, and an allyl cyanate to isocyanate rearrangement.
authors.affiliation: Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Liu
authors.forename: Robert
authors.initials: R
authors.lastname: Bittman
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D003485:Cyanates / Q000737:chemistry*; D005699:Galactosylceramides / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000498:Allyl Compounds; D003485:Cyanates; D005699:Galactosylceramides; D006027:Glycosides; D017953:Isocyanates; C493154:alpha-galactosylceramide