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Beilstein J. Org. Chem. 2014, 10, 1686–1691, doi:10.3762/bjoc.10.177
Graphical Abstract
Figure 1: Synthesized G0, G1 and G2 dendrons and functionalized saccharides used for carbonyl conjugation.
Scheme 1: Schematic depiction of dendron conjugation to saccharides by carbonyl chemistry.
Scheme 2: Synthesis of the dendrons.
Scheme 3: Dendron conjugation to fucose moieties by reductive amination. Reagents and conditions: a) 4, 3 M Na...
Scheme 4: Dendron conjugation to fucose via oxime ligation (buffer = citrate buffer).
Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58
Figure 1: Structure of trehalose (1), validoxylamine A (2), 1-thiatrehazolin (3), trehalostatin (4), casuarin...
Figure 2: Structure of nojirimycin-based (7, 8) and pyrrolidine-based (9) leads.
Figure 3: Structures of potential inhibitors 10–21.
Scheme 1: Synthesis of nojirimycin-based inhibitors 10,12 and 13. Reagents and conditions: (a) H2, Pd/C, NH4O...
Scheme 2: Synthesis of pyrrolidine derivatives 14, 16, 17 and 19. Reagents and conditions: (a) H2, Pd(OH)2/C,...
Scheme 3: Synthesis of pyrrolidines 20 and 21. Reagents and conditions: (a) H2, Pd/C, MeOH, HCl; (b) octanal,...
Figure 4: Histogram of the inhibitory activity of compounds 7–10, 12–14, 16 and 20. Derivatives 10, 14 and 16...