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Biologically active glycosides from asteroidea, XXVI. Stereochemistry of the four diastereomers of ceramide and ceramide lactoside

✍ Scribed by Sugiyama, Shigeo ;Honda, Masanori ;Higuchi, Ryuichi ;Komori, Tetsuya

Book ID
102902348
Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
867 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The diastereomeric ceramides, (2__S__,3__S__,4__R__)‐, (2__S__,3__S__,4__S__)‐, (2__S__,3__R__,4__S__)‐, and (2__S__,3__R__,4__R__)‐2‐[(2__R__)‐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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