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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.