Abstract
Two members of a new class of anti conformationally locked 2'-deoxynucleoside mimics were synthesized starting from uridine through key 1-(β-D-arabinofuranosyl)uracil-6-carboxaldehyde intermediates. O5'-Mesylation of 1-(β-D-arabinofuranosyl)uracil-6-carboxaldehyde (5c) followed by pyridine-mediated transglycosidic displacement by the dominant 7,O2'-cyclic hemiacetal gave the locked 2',5'-dideoxyuridine mimic (7). Transglycosidic transacetalation in the 7,O2'-cyclic hemiacetal of 1-(5-deoxy-5,5-dimethoxy-β-D-arabinofuranosyl)uracil-6- carboxaldehyde (18) gave the locked O5'-methyl-2'-deoxyuridine mimic (6b). These transglycosidic dioxomethine tether constructions involve proximity-assisted displacement reactions and provide an entry into new, highly biomimetic, anti conformationally locked 2'- deoxynucleoside mimics for use as probes of conformation-activity relationships.
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