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Global deprotection to furnish S. pneumonia serotype 12F repeating unit hexasaccharide 1. Reagents and conditions: (a) thioacetic acid, pyridine, rt, 65%; (b) Zn, AcOH/Ac2O/THF, Cu2SO4 (aq, decomposed); saponification conditions that lead to β-elimination (c) i. NaOMe (0.5 M in MeOH) in MeOH, ii. NaOH (4 M, 2 M, 1 M, 0.5 M, 0.1 M) solution in THF, iii. H2O2, LiOH, THF, H2O; successful sequence (d) Pd/C, AcOH, H2O, t-BuOH (e) H2O2, LiOH, THF, H2O, 37% over two steps.
