79366-24-8

Basic information

• Product Name: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine
• Synonyms: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine
• CAS NO: 79366-24-8
• Molecular Weight: 564.554
• Mol File: 79366-24-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(79366-24-8)
• EPA Substance Registry System: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(79366-24-8)

Safety Data

• Hazardous Substances Data: 79366-24-8(Hazardous Substances Data)

Upstream product

• 15373-23-6 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 1526929-34-9 C₃₁H₂₆N₆O₇ 
• 3510-73-4 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 120-73-0 purine 

Downstream Products

• 550-33-4 Nebularin 
• 1512860-68-2 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-cyclohexyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 

Relevant articles and documents

Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water

A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

Syntheses of 9-β-D-Ribofuranosylpurine (Nebularine) and Its Analogues

9-β-D-Ribofuranosylpurine (nebularine) (9) has been synthesized by two methods. (i) 2,6-Dichloro-2',3',5'-tri-O-benzoyl-9-β-D-ribofuranosylpurine (7) on dehalogenation followed by debenzoylation using methanolic ammonia affords nebularine (9). (ii) 6-Chloro-2',3',5'-tri-O-acetyl-9-β-D-ribofuranosylpurine (18) on dehalogenation followed by deacetylation yields 9.Nebularine analogues , 9-β-D-xylofuranosylpurine (12) and 9-α-L-rhamnopyranosylpurine (15) have also been synthesized from 2,6-dichloro-2',3',5'-tri-O-acetyl-9-β-D-xylofuranosylpurine (10) and 2,6-dichloro-2',3',4'-tri-O-benzoyl-9-α-L-rhamnopyranosylpurine (13).Dehalogenation of 10 and 13 followed by deacetylation and debenzoylation with methanolic ammonia affords 12 and 15 respectively.