Synthetic studies on glycosphingolipids from Protostomia phyla: total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis.
Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).
Yamamura
Takeshi
T
Kyoritsu University of Pharmacy, Shibakoen 1-5-30, Minato-ku, Tokyo 105-8512, Japan.
Hada
Noriyasu
N
Kaburaki
Asuka
A
Yamano
Kimiaki
K
Takeda
Tadahiro
T
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D048210:Echinococcus multilocularis / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry
D006028:Glycosphingolipids; D009844:Oligosaccharides