Tetrahedron
Tetrahedron
5 years ago

Synthesis of glycosphingolipids from the fungus Hirsutella rhossiliensis

Synthesis of glycosphingolipids from the fungus Hirsutella rhossiliensis
The total synthesis of two neutral glycosphingolipids (GSLs) from the fungus Hirsutella rhossiliensis has been achieved. The GSLs possess a common neogala-core (Galβ1-6Gal) and have the following sequence: α-d-Manp(1 → 3)-β-d-Galp(1 → 6)-β-d-Galp(1 → 6)-β-d-Galp(1↔1)Cer (1) and α-d-Manp(1 → 3)-β-d-Galp(1 → 6)[α-d-Glcp(1 → 4)]-β-d-Galp(1 → 6)-β-d-Galp(1↔1)Cer (2). Our efficient synthetic strategy uses the different reactivity of the hydroxyl groups of galactose and the α-orienting solvent effect of dioxane-toluene to generate GSLs (1) and (2).

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017310621

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