A building block approach to the synthesis of a family of S-linked alpha-1,6-oligomannosides
Tyson Belz, Spencer J Williams
CARBOHYDRATE RESEARCH | ELSEVIER SCI LTD | Published : 2016
The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasacch..View full abstract
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Awarded by Australian Research Council (ARC)
We thank the Australian Research Council (ARC) for funding support (FT130100103). SJW is an ARC Future Fellow.