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. Author manuscript; available in PMC: 2015 Jun 1.
Published in final edited form as: Chem Sci. 2014 Mar 31;5(6):2398–2406. doi: 10.1039/C4SC00451E

Scheme 1. Synthesis of Compounds 3-22.

Scheme 1

Conditions and Reagents: i) CTP, N. Meningitidis CMP-NeuAc Synthetase, P. Damsella α2,6 Sialyltransferase. Yield: (C) = 98%, (D) = 90%. ii) For X = Cl, MeOH, CH2Cl2, NEt3. For X = N-hydroxysuccinimide, DMF, H2O, NaHCO3. iii) For R = NHCbz: Pd/C, H2, H2O. Yields: 77-92% over 2 steps. For R = N3: PMe3, THF, H2O. Yields 70-75% over 2 steps. iv) (A), Pyruvate, C. Perfringens NeuAc Aldolase, CTP, N. Meningitidis CMP-NeuAc Synthetase, P. Damsella α2,6 Sialyltransferase. Yield: 96%. v) H2O, MeOH, I2, pH 1.0. Yield: 75%. vi) DMF, NEt3. Yield: 86%. vii) PMe3, THF, H2O. Yield: 97%. viii) DMF, H2O, NaHCO3. Yield: 73%. ix) Pd/C, H2, H2O. Yield: 90%.