1609453-79-3Relevant academic research and scientific papers
Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides
Siciliano, Carlo,Barattucci, Anna,Bonaccorsi, Paola,Di Gioia, Maria Luisa,Leggio, Antonella,Minuti, Lucio,Romio, Emanuela,Temperini, Andrea
, p. 5320 - 5326 (2014/06/23)
A total synthesis of d-erythro-sphinganine [(2S,3R)-2-aminooctadecane-1,3- diol] starting from commercial N-tert-butyloxycarbonyl-l-serine methyl ester is described. The approach is based on the completely stereoselective preparation of an α-amino epoxide obtained by treating a protected l-serinal derivative with dimethylsulfoxonium methylide. The oxirane synthon is obtained with an anti configuration fitting the (2S,3R) stereochemistry of the 2-amino-1,3-diol polar head of d-erythro-sphinganine. The synthetic procedure afforded the target compound in a 68% overall yield based on the initial amount of the starting l-serine material.
