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Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue
Authors:Xuequan Lu
Institution:Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, NY 11367-1597, USA
Abstract:The title compounds (1, 2) were synthesized from (2R,3S)-2-O-benzyl-3,4-O-(3′-pentylidene)-2,3,4-trihydroxybutanal (5). Installation of the E-double bond and aliphatic chain into the sphingosine base was effected by a sequence of Horner-Wadsworth-Emmons olefination of 5, conversion to allylic acetate 8, and copper-mediated Grignard coupling. The method is versatile, allowing a broad variety of aliphatic chains to be introduced in the organocuprate coupling step.
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