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A) Mechanism of 1,2-cis stereoselective glycosylation using ManA donors. Once the ManA donor is activated, the C-5 carboxylate stabilizes the oxocarbenium ion in a 3H4 conformation which favors formation of β-ManA linkages. B) Series of β(1–4)-oligomannuronates synthesized using AGA and ManA donors. The AGA cycle includes coupling (TfOH) and Lev deprotection (hydrazine). C) β(1–4)-Man and β(1–4)-ManA oligosaccharides prepared using fluorous-tag (FTag) assisted automated synthesis.
