287381-77-5

Upstream product

• 287381-75-3 (1S,2S,3R,4R,1'R)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene 
• 88303-25-7 tetradecylmagnesium bromide 
• 287381-76-4 (1S,2S,3R,4R,1'R)-2-(t-butyldiphenylsilyloxymethyl)-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene 

Downstream Products

• 287381-79-7 (2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol 
• 287381-78-6 (2S,3E)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3-octadecene 
• 1026173-04-5 2,2,2-Trichloro-acetimidic acid (R)-1-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-pentadecyl ester 

Relevant academic research and scientific papers

Enantioselective synthesis of lyxo-(2R,3R,4R)-C18-phytosphingosine using double stereodifferentiation

lyxo-C18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-β and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C18-phytosphingosine with high diastereoselectivity (de=94%) and excellent enantioselectivity (ee=93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. Copyright (C) 2000 Elsevier Science Ltd.