A total synthesis of o-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 alpha-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
Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides / Siciliano, Carlo; Barattucci, A.; Bonaccorsi, P.; DI GIOIA, Maria Luisa; Leggio, Antonella; Minuti, L.; Romio, E.; Temperini, A.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 79:11(2014), pp. 5320-5326.
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Titolo: | Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides |
Autori: | |
Data di pubblicazione: | 2014 |
Rivista: | |
Citazione: | Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides / Siciliano, Carlo; Barattucci, A.; Bonaccorsi, P.; DI GIOIA, Maria Luisa; Leggio, Antonella; Minuti, L.; Romio, E.; Temperini, A.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 79:11(2014), pp. 5320-5326. |
Handle: | http://hdl.handle.net/20.500.11770/138259 |
Appare nelle tipologie: | 1.1 Articolo in rivista |