Synthesis of d -erythro-Sphinganine through Serine-Derived α-Amino Epoxides
| Autor: | Maria Luisa Di Gioia, Emanuela Romio, Anna Barattucci, Paola Bonaccorsi, Carlo Siciliano, Andrea Temperini, Lucio Minuti, Antonella Leggio |
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| Rok vydání: | 2014 |
| Předmět: |
Stereochemistry
Epoxide TMC-95A ANALOGS chemistry.chemical_compound Sphingosine CHEMISTRY Serine ASYMMETRIC-SYNTHESIS HIGHLY STEREOSELECTIVE-SYNTHESIS ONE-POT PROCEDURE SPHINGOLIPID METABOLISM Chemistry Organic Chemistry Synthon Enantioselective synthesis Diastereomer Total synthesis Stereoisomerism ALCOHOLS ACIDS DIASTEREOSELECTIVE SYNTHESIS Yield (chemistry) Epoxy Compounds Stereoselectivity PHYTOSPHINGOSINE Derivative (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 79:5320-5326 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo500493c |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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