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Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152
Graphical Abstract
Figure 1: Target ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones 1‒3.
Figure 2: Molecular representation of the best binding poses of the four compounds with the predicted highest...
Scheme 1: Reagents and conditions: a) 1. (BnO)2P-NMe2, 1H-tetrazole, 0 °C→rt, 1 h, 2. m-CPBA, 0 °C→rt, 1.5‒2 ...
Scheme 2: Reagents and conditions: a) PivCl, pyridine, CH2Cl2, rt, overnight; b) BnBr, NaOH, TBAB, THF, reflu...
Scheme 3: Reagents and conditions: a) EtSH, BF3∙OEt2, CH2Cl2, 0 °C, 2 h; b) 1. (BnO)2P-NMe2, 1H-tetrazole, 0 ...
Scheme 4: Reagents and conditions: a) PhSH, or iPrSH, BF3·OEt2, CH2Cl2, −5 °C, 1 h; b) BF3·OEt2, Ac2O, 0 °C, ...
Scheme 5: Reagents and conditions: a) 1. (BnO)2P-NMe2, 1H-tetrazole, 0 °C→rt, 1 h, 2. m-CPBA, 0 °C→rt, 1.5‒2 ...
Figure 3: TLC analysis of the effects of the target compounds at 500 μM on the production of lower lipid-link...
Figure 4: TLC analysis of the dose effects of the compounds 1bα and 3a on production of lower lipid-linked ga...