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Beilstein J. Org. Chem. 2017, 13, 1533–1541, doi:10.3762/bjoc.13.153
Graphical Abstract
Figure 1: C-5’ configuration of nucleoside derivatives and related biological activity.
Scheme 1: Synthesis of alcohols 1–5.
Scheme 2: Synthesis of propargylic alcohols 11–15 and their partial or complete deprotection.
Scheme 3: Synthesis of reference compounds and strategy for assignment of C-5’ configuration.
Figure 2: 1H NMR of (5’R)-16 and (5’S)-16 and of a (5’R)/(5’S)-16 mixture.
Figure 3: 1H NMR of (5’R)-17 and (5’S)-17 and example of configuration determination for a pure isolated comp...
Figure 4: Hypothetical Cram chelated models.
Figure 5: Proposed stereochemical models.
Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12
Figure 1: Sugars, iminosugars and carbasugars.
Figure 2: Retrosynthetic analysis.
Scheme 1: Reagents and conditions: (a) OsO4, NMO, tBuOH, rt; (b) TFA, H2O, rt.
Scheme 2: Reagents and conditions: (a) mCPBA, CH2Cl2, NaHCO3, rt; (b) see text.
Scheme 3: Reagents and conditions: (a) i : SOCl2, Et3N, CH2Cl2, 0°C; ii : RuCl3, NaIO4, CCl4, CH3CN, 0°C to r...
Figure 3: 1D proton NMR spectra of the C8 ring in compound 11 (upper) and the simulated signals (down) on the...
Figure 4: Schematic representation of the NOEs (indicated with arrows) found to deduce the structure of 11. B...
Figure 5: X-ray structure of epoxide 7 (upper) and sulfate 9 (down) solved using SHELXS and anisotropically r...