79366-24-8

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 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 120-73-0 purine 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

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.