Studies on Chemotherapeutic Agents.I. A Synthesis of Pyrimidine Nucleosides of D-glucuronic Acid and Its Derivatives

Silane promoted glycosylation and its applications for synthesis of sugar compounds and active pharmaceutical ingredients (APIs)

“…With a 95% yield, the glycoside product (45) was produced with perfect control over anomeric structure. Using the identical hydroxyketone (42) and mannosilane (44), a nickel-catalyzed siteselective hydrosilylation yielded product (46) in 80% tethering yield with a 6 : 1 diastereoselectivity. The syntheses of landomycin A and D by Yu and coworkers are an example (Scheme 14) of such reactions.…”

“…This a-configuration was identified on the finally isolated a-elvucitabine (Scheme 23). 44 Routes for the synthesis of uronic acid based nucleosides bearing nitrogenous bases like pyrimidine, 45 uracil, 46 cytosine, 47 and purine [48][49][50][51] employ the N-glycosylation of silylated nucleobases with glucuronyl donors such as glycosyl halides, 1-O-acetyl donors, 47b or methyl glycosides, 51 and the oxidation of the C-5 0 hydroxy group of nucleosides. pyranosyl-glucuronoamides synthesized from glucofuranurono-6,3-lactone and triacetylated glucofuranurono-6,3-lactone, were exploited as glycosyl donors for the microwave-assisted Lewisacid-promoted coupling to the silylated nucleobase.…”

Synthesis of Purine Nucleosides from D‐Glucuronic Acid Derivatives and Evaluation of Their Cholinesterase‐Inhibitory Activities

“…Treatment of the uronate‐based nucleoside with methanolic ammonia gave the corresponding glucuronamide‐containing nucleoside. Uronic acid, uronate, or uronamide‐based nucleosides bearing pyrimidine,10 uracil,11 cytosine,11 and purine,12–15 moieties have been synthesized, and some of these compounds were found to have significant biological activities. Methods for their synthesis involve the N ‐glycosylation of silylated nucleobases with glucuronyl donors such as glycosyl halides, 1‐ O ‐acetyl donors,11b,12 or methyl glycosides,15 and the oxidation of the C‐5′ hydroxy group of nucleosides 11c,16.…”

Glucuronyl C4 dehydrogenation by the radical SAM enzyme BlsE involved in blasticidin S biosynthesis

“…To this end, cytosylglucuronamide (CGM) (Fig. 1), 28 an amide analog of CGA, was synthesized to test the BlsE activity. The reaction was then performed by incubation of the reconstituted BlsE with SAM, CGM, and sodium dithionite (DTH), and the reaction mixture was analyzed by liquid chromatography with high-resolution mass spectrometry (LC-HRMS).…”