89873-10-9

Upstream product

• 23316-67-8 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 
• 82225-19-2 2,3,5-tri-O-acetyl-β-D-ribofuranosyl cyanide 

Downstream Products

• 89873-13-2 ethyl 3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-thiadiazole-5-carboxylate 
• 89873-15-4 ethyl 3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)isothiazole-4-carboxylate 
• 89873-14-3 ethyl 3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)isothiazole-5-carboxylate 
• 158227-08-8 C₂₇H₂₂BrNO₈ 
• 89873-12-1 5-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxathiazol-2-one 

Relevant academic research and scientific papers

Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixture

Action of nitrile hydratase from Rhodococcus rhodochrous IFO 15564 on derivatives of 2,5-anhydro-D-allononitrile

The conversion of 2,5-anhydro-D-allononitrile derivatives by a nitrile hydratase from Rhodococcus rhodochrous IFO 15564 was studied. The activity of the enzyme was strongly effected by the steric bulkiness of the substituents at the 3-position of the substrates, and the corresponding amides were obtained in high yields from the nitriles with free hydroxyl groups at the 3- and 4-positions.

Stereoselective bromination of β-ribofuranosyl amide. Enantioselective synthesis of (+)-hydantocidin

The synthesis of hydantocidin, a potent herbicidal natural product, is highlighted by a stereoselective bromination of β-D-ribofuranosyl amide to give only the α-bromo β-amide and subsequent spirocyclization about the anomeric position with silver cyanate to form the hydantoin moiety.

C-Nucleosides: Synthesis of Novel Ribavirin Analogues by Cycloaddition Reactions of D-Allononitrile-N-sulfide

The preparation and synthetic application of O-benzoyl-protected 2,5-anhydro-D-allononitrile-N-sulfide was investigated.The O-benzoyl-protected 2,5-anhydro-D-allononitrile was hydrolyzed to the corresponding allonamide, which was converted to the protected 5-β-D-ribofuranosyl-1,3,4-oxathiazol-2-one.Generation of the nitrile sulfide by pyrolysis of the latter in the presence of ethyl cyanoformate and ethyl propiolate afforded thiadiazole and isothiazole carboxylate esters, which were elaborated to thiadiazole and isothiadiazole C-nucleoside analogues 3 and 4 of ribavirin.None of these compounds produced any significant inhibition either of in vitro L1210 cell growth or of viral replication in any of the tested systems.Analysis of the 1H NMR spectra of ribavirin and the C-nucleoside analogues 3 and 4 showed that the conformational equilibrium of the ribose moiety, which lies at the N side for ribavirin, is shifted toward the S conformers in the compounds 3 and 4.Ribavirin and compound 4 have a similar rotameric distribution at the C4'-C5' exocyclic bond, but compound 3 behaves differently.