Expedient Synthesis of the α-<i>C</i>-Glycoside Analogue of the Immunostimulant Galactosylceramide (KRN7000)

Abstract

[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.