Section 8
Chapter 7,062

Biologically active glycosides from asteroidea xxvi. stereochemistry of the four diastereomers of ceramide and ceramide lactoside

Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T.

Liebigs Annalen der Chemie 4: 349-356


DOI: 10.1002/jlac.199119910161
Accession: 007061242

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The diastereomeric ceramides (2S,3S,4R)-, (2S,3S,4S)-, (2S,3R,4S)-, and (2S,3R,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriols 5-8 and the corresponding ceramide lactosides 1-4 have been synthesized. Compound 1 is almost identical with the natural specimen, acanthalactoside A. The physical data of these diastereomeric compounds are most useful to determine the stereochemistry of ceramides and ceramide lactosides, either isolated from natural sources or obtained by partial hydrolysis of gangliosides.

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