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. Author manuscript; available in PMC: 2022 Oct 15.
Published in final edited form as: ACS Chem Biol. 2021 Sep 10;16(10):1908–1916. doi: 10.1021/acschembio.1c00268

Scheme 1.

Scheme 1.

Synthetic Route for the Preparation of 2-amino Muramic Acid: Scalable synthesis of 2-amino-muramic acid reported over 5 synthetic steps in 25% yield on a multigram scale. Reaction Conditions: (a) Cbz-OSu, NaHCO3, 1:1 THF:H2O (80%); (b) BnOH, AcCl, 80°C; (c) PhCH(OMe)2, pTSA, DMF (57% over 2 steps); (d) 60% NaH, (S)-(−)-2-Bromopropionic Acid, THF, −20°C (69%); (e) IRA H+ resin, MeOH, 60°C (58%); (f) H2, Pd(OH)2, 14:5:1 THF:H2O:AcOH (77%)