497084-66-9

Upstream product

• 497084-57-8 N-benzyloxycarbonyl-4(R)-[3'-oxo-(1'E)-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine 
• 124-10-7 methyl myristoate 
• 497084-65-8 dimethyl 2-oxopentadecanephosphonate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 117833-92-8 (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde 
• 117833-99-5 N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine 

Downstream Products

• 497084-70-5 (2R,5R)-2-[(benzyloxycarbonyl)amino]-(3E)-octadecene-1,5-diol 

Relevant academic research and scientific papers

Synthesis and growth inhibitory activity of chiral 5-hydroxy-2-N-acyl-(3E)-sphingenines: Ceramides with an unusual sphingoid backbone

The unusual sphingoid base 5-hydroxy-3-sphingenine was identified in the hydrolysate of brain sphingolipids more than 40 years ago. We present here the first synthesis of the 5R and 5S diastereoisomers of the N-acyl derivatives of 5-hydroxy-3-sphingenine, 2 and 3, respectively, which represent regioisomers of (2S,3R)-ceramide (1). The key steps include the synthesis of a,β-unsaturated ketone intermediates 4 and 5 from N-Cbz- and N-Boc -L-serine and diastereoselective reduction of the enones. The configuration at the new carbinol center was deduced by proton NMR analysis of (R)- and (S)-Mosher [methoxy(trifluoromethyl)phenylacetate] ester derivatives. Ceramide analogues 2 and 3 showed a markedly higher antiproliferative activity than 1 on MCF-7 cells.