Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).
[Structure: see text] Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf@pitt.edu
Pierce
Joshua G
JG
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D006027:Glycosides; D007097:Imines; C103873:KRN 7000