A Simple and Convenient Method for the Selective N-Acylations of Cytosine Nucleosides

Synthesis and Hybridization Ability of Oligodeoxyribonucleotides Incorporating N-Acyldeoxycytidine Derivatives

“…The key intermediates Ϫ 4-N-acyl-5Ј-O-(4,4Ј-dimethoxytrityl)deoxycytidine derivatives 3a؊c Ϫ required for incorporation of these N-acyldeoxycytidine derivatives into d(T 6 XT 6 ) were obtained in high yields by treatment of deoxycytidine hydrochloride (1) with the corresponding acid anhydride in the presence of triethylamine in DMF at 60°C for 6 h, [13] followed by in situ treatment of the resulting N-acylated products 2a؊c with 4,4Ј-dimethoxytrityl chloride in pyridine (Method A of Scheme 1).…”

Synthesis, Molecular Conformation and Activity Against Herpes Simplex Virus of (E)-5-(2-Bromovinyl)-2′-Deoxycytidine Analogs

“…The analogs N 4 -acetyl-BrVdCyd (2), N 4 -propanoyl-BrVdCyd (3), and N 4 -butanoyl-BrVdCyd (4) were prepared from BrVdCyd (1) via selective acylation of the amino group by dissolving the substrate in N,N-Dimethylformamide (DMF) at room temperature, followed by cooling the solution in ice under argon and adding the proper acylating agent according to a known procedure. [15] Reaction mixtures were checked by thin layer chromatography (TLC) after 24 hours, showing total consumption of starting material. The crude products were purified over a short plug of silica gel, checked for their purity, and submitted for biological testing.…”

Selective deacylation of peracylated ribonucleosides

“…Selective N-acylation of these moieties has been realized by (a) Direct chemoselective N-acylation of unprotected nucleosides using mild acylating agents such as aqueous benzoic anhydride. 10 This approach is restricted to cytidine nucleosides, as O-acylation typically accompanies N-acylation with other nucleosides. (b) Transient protection methodology, that is, a three-step process involving protection of free alcohol groups as silyl ethers, N-acylation and desilylation using a weak base.…”