Concise Syntheses of a-Galactosyl Ceramide, D-ribo-Phytosphingosine, and Ceramide.

Total syntheses of a-galactosyl ceramide, D-ribo-phytosphingosine, and ceramide through an a-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 a-linked disaccharide was subsequently transformed into a-galactosyl ceramide, phytosphingosine, and ceramide. [ABSTRACT FROM AUTHOR]