850223-33-5

Upstream product

• 753020-01-8 (R)-2-(benzyloxy)-2-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]ethanol 
• 753020-02-9 (2R,3S)-2-O-benzyl-3,4-O-(3'-pentylidene)-2,3,4-trihydroxybutanal 
• 15890-72-9 laurylmagnesium bromide 

Downstream Products

• 850223-34-6 (E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol 

Relevant academic research and scientific papers

Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue

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.