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Beilstein J. Org. Chem. 2023, 19, 282–293, doi:10.3762/bjoc.19.24
Graphical Abstract
Figure 1: Natural iminosugars (1,4-dideoxy-1,4-imino-ᴅ-mannitol (DIM) and swainsonine) and selected examples ...
Scheme 1: Synthesis of the key pyrrolidine 3 and the target pyrrolidines 7–10. Reagents and conditions: (a) M...
Scheme 2: Synthesis of the intermediate 13 and the target pyrrolidines 17–20. Reagents and conditions: (a) 1....
Scheme 3: Synthesis of the target pyrrolidines 26–29. Reagents and conditions: (a) Tf2O, pyridine, CH2Cl2, 0 ...
Figure 2: Superposition of the inhibitor 29 (green), docked into dGMII, with X-ray complexes of swainsonine (...
Figure 3: FMO-PIEDA total pair interaction energies (ΔElinker-E) (in kcal mol−1) between the structural moiet...
Figure 4: QM/MM optimized complexes 28:dGMII (top) and 31:dGMII (bottom) [22]. N-2-naphthylmethyl group (grey) an...
Figure 5: FMO-PIEDA total pair interaction energies (ΔElinker-E) (in kcal mol−1) between the N-2-naphthylmeth...
Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189
Figure 1: Structures of GMIIb inhibitors.
Scheme 1: Synthesis of pyrrolidines 2a and 3a.
Scheme 2: Synthesis of pyrrolidines 2b,c and 3b,c.
Scheme 3: Synthesis of pyrrolidines 4.
Scheme 4: Synthesis of pyrrolidines 5.
Figure 2: Molecular structure (OLEX2 drawing with adjacent ChemDraw image) of compound 20. Atomic displacemen...
Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51
Figure 1: Structures of vanillyl β-D-glucoside (1), salidroside (2) and isoconiferin (3).
Scheme 1: Reagents and conditions: a) Ac2O, pyridine, rt, 10 h, >98%; b) NaBH4, H3PO4, −5 °C, 85–95%.
Scheme 2: Reagents and conditions: a) Ac2O, H2SO4, 5 °C to rt, 30 min, >94%; b) 1. NaBH4, THF, 5 °C, 10 min, ...
Figure 2: Synthesized glycosyl donors.
Scheme 3: General reaction scheme for the synthesis of p-hydroxyphenylalkyl glycosides.
Figure 3: Overview of protected and deprotected products.