Zurückführung der Konfiguration des (natürlichen) Sphingosins auf die der D‐erythro‐2‐Amino‐3,4‐dioxy‐buttersäure. 12. Mitteilung über Sphingosin und Sphingolipoide

摘要: Sphingosine was cleaved by ozonolysis into 2-hydroxy-3-aminobutyrolactone-hydrochloride, this, in turn, hydrogenated two steps to a slightly levorotatory 2-amino-1, 3,4-butantriol. The latter proved be the antipode of amino-butantriol obtained on hydrogenation γ-lactone L-erythro-2-amino-3, 4-dihydroxy-butyric acid. Since configurations four stereoisomeric 2-amino-3,4-dihydroxy butyric acids have already been established, sphingosine belongs D-erythro-series. On other hand, trans-ethylenic structure having elucidated recently, D-erythro-2-amino-1,3-dihydroxy-4-trans-octadecene can assigned it. These findings and deductions agree well with pieces evidence regarding configuration dihydro sphingosine, reported previously Grob Carter, resp.