Azidosphingosine Glycosylation in Glycosphingolipid Synthesis

Abstract

Abstract The 3-O-protected azide derivatives of C18-sphingcsine s me 1A-1C reacted with O-acyl protected trichloroacetimidates of D-glucose, D-galactose, and laczose to afford the corresresponding β-glycosides in high yields. Ortho-ester formation in the case of O-acetyl compound could he avoided by increasing the amount of bcrcn trifluoride diethyl ether catalyst. Deprotection. and azido group reduction provided the psychosines of D-gluccse, D-galactose, and lactose (5, 10, and 15), which are versatile intermediates for the attachment of different fatty acii residues. With hexadecanoyl chloride, for instance, the corresponding glycosphingolipids 6, 11, and 16, respectively, were obtained.