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Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79
Graphical Abstract
Figure 1: Structure of glycyrrhizin (GL), carbenoxolone (CBX), and spacer analogues.
Scheme 1: Synthesis of methyl 2-haloethyl 1-thio-glucuronide derivatives: (a) 1 M NaOMe, MeOH, −60 °C to −45 ...
Scheme 2: Synthesis of thioalkylglucuronide GA derivatives: (a) DMF, DIPEA, 45–50 °C, 16 h, 79%; (b) TEA, Ac2...
Figure 2: 400 MHz 1H NMR expansion plots of the carbohydrate region of compound 11, recorded at various tempe...
Scheme 3: Synthesis of 3-thioether-bridged glucuronide derivatives: (a) K2CO3, acetone, 60%; (b) 0.8 M NaOMe,...