Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes

The first total synthesis of a novel α-galactoglycosphingolipid clarhamnoside has been achieved through a straightforward strategy. A thiogalactosyl donor with a benzylidene group at C-4 and C-6 and nonparticipating p-methoxybenzyl group at C-2 was successfully employed in the stereocontrolled syntheses of α-GalGSLs. The N-Phth-protected trifluoroacetimidate donor for terminal disaccharide was successfully applied in constructing the [GalNAcβ-(1→6)-Gal] glycosidic linkage.

Graphical abstractClarhamnoside, a novel spongal α-GalGSL identified from new specimens of Agela clathrodes, has been first synthesized through a straightforward strategy.Figure optionsDownload full-size imageDownload as PowerPoint slide