Nucleophilic substitution at C3′ of 1‐(2‐deoxy‐5‐O‐trityl‐β‐D‐erythr‐pentofuranosyl)‐2‐methoxy‐5‐methyl‐4(1H)‐pyrimidinone (5) with methyl iodide/triphenylphosphine/diethyl azodicarboxylate gave the expected inverted iodide 6 and minor epimer 7. Treatment of 6 with lithium nitrite/phloroglucinol yielded the desired nitro derivative 8 and subsequent acidic deprotection afforded the title compound 1. This represents a novel method for the introduction of a nitro group into the furanosyl moiety of a nucleoside. The nmr spectroscopic techniques (COSY, NOESY, nOe, HMQC and HMBC) were used to determine the stereochemistry at C3′ of the nucleosides. Spectral analysis of H‐D exchange at the 3′‐position of 1 did not indicate the formation of its epimer 10.

No abstract

No abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

No abstract