Abstract
Total synthesis of the ganglioside Hp-s1 1, which was identified from the ovary of sea urchin Diadema setosum and displays neuritogenic activity is described. The characteristic sequence of the disaccharide part was efficiently assembled by coupling of a highly active benzyl protected glucosyl donor and a phytosphingosine derived acceptor with high stereoselectivity, leaving the primary hydroxyl group of the glucoside acceptor free for further glycosylation. The corresponding disaccharyl acceptor was directly glycosidated with the acetyl-protected sialyl donor part to afford the trisaccharide in high yield and stereoselectivity. After amidization formation and global deprotection, ganglioside Hp-s1 1 was obtained.
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