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Synthesis of α-4-N-Ac-Sia-2Me. (A) Overview of the synthesis. (Step i) a. Dowex 50wx8, MeOH; b. Ac2O, AcOH, H2SO4, 61% over two steps; (step ii) a. TMSN3, t-BuOH; b. NBS, MeOH, 44% over two steps; (step iii) a. tributyltin hydride, AIBN, 1,4-dioxane; b. Ac2O, NEt3, THF; c. NaOH, MeOH/H2O, 27% over three steps. (B) 1H-NMR spectrum of final compound.
