Concise Syntheses of α-Galactosyl Ceramide, d-ribo-Phytosphingosine, and Ceramide

Abstract

Total syntheses of α-galactosyl ceramide, d-ribo-phytosphingosine, and ceramide through an α-galactosyl phytosphingosine derivative as a common synthon were accomplished in overall yields of 26%, 15%, and 20% in nine, seven, and eight steps, respectively, starting from an acetonide-protected d-lyxose derivative. This short and efficient protocol involved protection and glycosylation of the acetonide-protected d-lyxose with d-galactosyl iodide as a key step. The resulting α-linked disaccharide was subsequently transformed into α-galactosyl ceramide, phytosphingosine, and ceramide.

Key words

glycosylations - glycolipids - total synthesis

• References

• 1 Yu-Fen Yen and R. C. Sawant contributed equally to this work.
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