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Two types of sulfated octyl tetra- to octaoligofucosides with different sulfation patterns were synthesized employing a combination of stepwise elongation and convergent strategies in which trichloroacetimidates and thioglycosides were selected as the glycosyl donors.
The first total synthesis of caminoside B, a novel marine antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia, was developed. This marine small molecule inhibitor (IC 50 =20μM) targeting type III secretory pathway of bacterial pathogenesis was assembled in good yield via a ‘2+2+1’ strategy based on stereocontrolled construction of the four glycosidic linkages.
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