ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Sphingosine was cleaved by ozonolysis into 2-hydroxy-3-aminobutyrolactone-hydrochloride, this, in turn, hydrogenated in two steps to a slightly levorotatory 2-amino-1, 3,4-butantriol. The latter proved to be the antipode of the amino-butantriol obtained on hydrogenation of the γ-lactone of L-erythro-2-amino-3, 4-dihydroxy-butyric acid. Since the configurations of the four stereoisomeric 2-amino-3,4-dihydroxy butyric acids have already been established, sphingosine belongs to the D-erythro-series. On the other hand, the trans-ethylenic structure of sphingosine having been elucidated recently, the structure of D-erythro-2-amino-1,3-dihydroxy-4-trans-octadecene can be assigned to it. These findings and deductions agree well with other pieces of evidence regarding the configuration of dihydro sphingosine, reported previously by Grob and Carter, resp.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19540370515
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