title: Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.
abstract: [reaction: see text] Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.
authors.affiliation: Department of Chemistry, Hunter College of CUNY, 695 Park Avenue, New York, New York 10021, USA.
authors.forename: Guangwu
authors.initials: G
authors.lastname: Chen
authors.forename: John
authors.initials: J
authors.lastname: Schmieg
authors.forename: Moriya
authors.initials: M
authors.lastname: Tsuji
authors.forename: Richard W
authors.initials: RW
authors.lastname: Franck
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000276:Adjuvants, Immunologic; D000475:Alkenes; D005030:Ethylenes; D005699:Galactosylceramides; D006027:Glycosides; D014753:Vinyl Compounds; C036216:ethylene; D013110:Sphingosine