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Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162
Graphical Abstract
Figure 1: Chemical structures of hexa-acylated Escherichia coli lipid A, monophosphorylated lipid X (the redu...
Scheme 1: Enantioselective synthesis of Nap-protected (R)-3-hydroxytetradecanoic acid (7). Conditions: (a) Me...
Scheme 2: Synthesis of monoacylated glucosamine building blocks. Conditions: (a) NaHCO3, TrocCl, H2O, 0 °C, 9...
Scheme 3: Synthesis of lipid X monosaccharide 1. Conditions: (a) Zn, AcOH, CH2Cl2, rt; (b) acid 7, EDC·HCl, D...
Scheme 4: Synthesis of the disaccharide lipid A precursor 2. Conditions: (a) TfOH, 4 Å MS, dry CH2Cl2, 94%; (...