Abstract
Glycals were converted into thioethyl glycosyl donors through 1,2-anhydrosugar intermediates. Various participating groups in the C-2 position were examined for formation of β-glucosyl, β-galactosyl, and α-mannosyl linkages. A number of disaccharides was prepared employing a novel coupling protocol involving thioethyl 2-pivaloyl glycosyl donors and glycal acceptors. Using this methodology, a linear tetrasaccharide containing exclusively β-glucosyl-(1→4) linkages was prepared in high yields. Ready application to α-mannosylation and C2 branching are other hallmarks of the method.
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