74134-93-3

Upstream product

• 1415646-62-6 1-deoxy-1-ethynyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropyridene-β-D-ribofuranose 
• 58918-66-4 (2,3-O-isopropylidene-β-D-ribofuranosyl)acetylene 
• 141979-56-8 1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 74134-96-6 2-phenyl-4-(2,3-O-isopropylidene-β-D-ribosyl)-2H-1,2,3-triazole 
• 21090-79-9 3,6-anhydro-D-allo-2-heptulose phenylosazone 

Downstream Products

• 78548-27-3 2-phenyl-4-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-1,2,3-osotriazole 

Relevant academic research and scientific papers

Functionalization of 2H-1,2,3-Triazole C-Nucleoside Template via N2 Selective Arylation

C-Nucleosides are an underexplored and important class of nucleosides with antiviral and anticancer activity. In addition, triazole heterocycles are well employed as a strategy to modify nucleobase in nucleoside analogues, although rare examples were described for triazoyl C-nucleosides. N2-Aryl-1,2,3-triazole C-nucleoside compounds that could be obtained by selective 1,2,3-triazole heterocycle N2 arylation in 1-β-d-ribofuranosyl-2H-1,2,3-triazole substrate were designed in this study. The optimized condition used AdBrettPhos/[PdCl(allyl)]2 as the catalyst system. This transformation was accomplished by aryl halides bearing an electron donor and withdrawing groups, as well as by heterocyclic halides in good to excellent yields. The transformation developed in this study represents a significant contribution to the nucleoside field, once it allows for the synthesis of unexplored scaffolds through selective functionalization of triazole nucleosides.

STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-altro-2-HEPTULOSE PHENYLOSAZONE

Dehydration of D-altro-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro-osazone derivatives (2 and 3).Compound 3 was obtained as the preponderant isomer, with inversion at C-1 (C-3 of the starting osazone), and 2 was obtained without inversion.Refluxing of 3 with copper sulfate afforded the C-nucleoside analog, namely, 2-phenyl-4-β-D-ribofuranosyl-1,2,3-osotriazole (4).Acetylation of 4 afforded the tri-O-acetyl derivative 5.The anomeric configuration was determined by c.d. and n.m.r. spectroscopy.The mass spectra of compounds 2-5 are discussed.