Ceramide-1-phosphate sugars: new types of glycophospholipids.

Ceramide-1-phosphate sugars were synthesized by direct glycosyl phosphite/phosphate and O-glycosyl trichloroacetimidate/phosphate exchange reactions, respectively. Thus, ceramide-1-O-phosphoric acid 5 gave with sialyl phosphite 1 as sialyl donor directly beta-linked sialyl phosphate 6; deprotection afforded the corresponding glycophospholipid ceramide-1-phosphate N-acetylneuraminate 7. Similarly, from O-glucosyl- and O-galactosyltrichloroacetimidate 10 and 13 with phosphoric acid derivative 5 glycosyl ceramide-1-phosphate sugars 12 and 15, respectively, were obtained.