Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.
[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.
Chen
Guangwu
G
Department of Chemistry, Hunter College of CUNY, 695 Park Avenue, New York, New York 10021, USA.
Schmieg
John
J
Tsuji
Moriya
M
Franck
Richard W
RW
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
D000276:Adjuvants, Immunologic; D000475:Alkenes; D005030:Ethylenes; D005699:Galactosylceramides; D006027:Glycosides; D014753:Vinyl Compounds; C036216:ethylene; D013110:Sphingosine