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. 2006 Jul 20;8(15):3375-8.
doi: 10.1021/ol0613057.

Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)

Peter Wipf  1 , Joshua G Pierce
Affiliations

Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)

Peter Wipf et al. Org Lett. .

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.

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