Synthesis of 5‐Alkynyl Substituted 2ʹ‐Arabinosyl 2ʹ‐Halogenated Uridine Nucleosides

Abstract

This unit describes the detailed preparation of 5‐alkynyl‐2ʹ‐halogenated arabinosyl uridine nucleosides (2ʹ‐halo‐ara‐EdU) from uridine. These compounds were synthesized as prospective chemical probes for the detection of DNA synthesis in proliferating cells. Currently, this is the only synthetic methodology reported to access these compounds. The key to success of the synthetic approach was to employ a 3‐N‐nitro‐protecting group to stabilize the required 2ʹ‐triflate nucleoside precursor toward nucleophilic substitution. Several synthetic challenges were overcome to accommodate the combination of a 5‐alkyne and 3‐N‐nitro functional group, including facile introduction and removal of the N‐nitro group, and removal of the sugar acetyl groups under acidic conditions. © 2019 by John Wiley & Sons, Inc.

Synthesis, characterization and photophysical studies of dual-emissive base-modified fluorescent nucleosides

“…The structures of all the known compounds were confirmed by comparison of their spectral data with those reported in the literature. 32,37,38,44,45 The structures of the newly synthesized compounds 6a–f , 12a–f , 13a–f , 14a–f and 15a–f were unambiguously established on the basis of their spectral (IR, 1 H-NMR, 13 C-NMR, 1 H– 1 H COSY NMR, 1 H– 13 C HETCOR NMR, NOESY NMR, DEPT-135 NMR and HRMS) data analysis. The hydroxyl groups present in the sugar moiety of the target compounds 14a–f and 15a–f were confirmed by 1 H NMR spectra using D 2 O exchange experiments (see the ESI‡).…”