Synthesis of the Reducing‐end Hexasaccharide Fragment of Marine Lipopolysaccharide Axinelloside A

Abstract

Chemical synthesis of an orthogonally protected hexasaccharide relevant to the reducing‐end half of axinelloside A, a highly sulfated marine lipopolysaccharide, is disclosed. The synthesis features preparation of the scyllo‐inositol unit via a Ferrier‐type‐II rearrangement, construction of the 1,2‐cis‐glycosidic bonds via remote participation, and concise [2+2+2] assembly via Au(I)‐catalyzed glycosylation.