Some Stereochemical Aspects of Sphingosines and Phytosphingosines

After the first structural representation of this long-chain, amino alcohol had been proved erroneous, Carter and coworkers6,7 proposed the correct structure, namely, 2-amino-4-octadecene-l,3-diol (2). 

The geometry of the double bond of sphingosine and of some natural sphingosine derivatives has been elucidated.9-11 The dia-stereoisomeric relationship of the amino and 3-hydroxyl groups is erythro this was proved by degradation and synthesis.12 

Sphingosines and dihydrosphingosines do not exist in the free state in animals, plants, or micro-organisms. 

Configurational Correlation of C18-Sphingosine with D-Clucose (D-Glyceraldehyde) and L-Serine 

The degradation of N-acetyl-di-0-acetyl-CI8-sphingosine (4) with ozone gives13,14 3-amino-2-hydroxybutyrolactone (5) and tetra-decanal (6). 

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