51549-15-6

Basic information

• Product Name: Adenosine, 2',3',5'-tribenzoate
• CAS NO: 51549-15-6
• Molecular Formula: C31H25N5O7
• Molecular Weight: 579.569
• Mol File: 51549-15-6.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Adenosine, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, 2',3',5'-tribenzoate(51549-15-6)
• EPA Substance Registry System: Adenosine, 2',3',5'-tribenzoate(51549-15-6)

Safety Data

• Hazardous Substances Data: 51549-15-6(Hazardous Substances Data)

Upstream product

• 93-97-0 benzoic acid anhydride 
• 58-61-7 adenosine 
• 62374-23-6 N⁶,N⁶,2',3',5'-pentabenzoyl-β-D-adenosine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 129835-18-3 (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-3-ol 
• 98-88-4 benzoyl chloride 
• 958-09-8 2'-deoxy-D-adenosine 
• 613-90-1 benzoyl cyanide 
• 18055-47-5 N-Benzoyl-N,9-bis(trimethylsilyl)adenin 
• 151867-55-9 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl methyl carbonate 
• 4005-49-6 N-benzoyladenine 
• 4005-49-6 N₆-benzoyladenine 
• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 73-24-5 7H-purin-6-ylamine 

Downstream Products

• 1403611-75-5 (2R,3R,4R,5R)-2-(6-amino-8-cyclohexyl-9H-purin-9-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 154971-65-0 2',3',5'-tri-O-benzoyladenosine 6-N-(O,O-bis(2-cyanoethyl)phosphoramidate) 
• 58-61-7 adenosine 
• 15262-12-1 ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl benzoate 
• 62374-24-7 (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-((benzoyloxy)methyl)-4-hydroxytetrahydrofuran-3-yl benzoate 
• 5536-17-4 arabinosyl adenine 

Relevant articles and documents

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Fluorinated nucleoside 1 is a key starting material in the synthesis of rovafovir etalafenamide (2), a novel nucleotide reverse transcriptase inhibitor under development at Gilead Sciences for the treatment of HIV. While an initial manufacturing route enabled the production of 1 to support clinical development, alternative approaches were explored to further enhance manufacturing effectiveness, improve processing time, reduce cost, and minimize the environmental impact. Toward this end, two new routes were developed to a key synthetic intermediate, which was converted to 1 using a new protecting group strategy. The new chemistry led to improvements in the manufacturing process while reducing the overall process mass intensity (PMI).

An efficient approach to the synthesis of nucleosides: Gold(I)-catalyzed N-glycosylation of pyrimidines and purines with glycosyl ortho-alkynyl benzoates

Persuaded with gold: The title reaction in the presence of [Ph 3PAuNTf2] (Tf=trifluoromethanesulfonyl) led conveniently to the corresponding nucleosides with excellent regioselectivity (see scheme). Even purine derivatives underwent this transformation owing to the mild conditions, which enabled the use of protecting groups that would not usually be compatible with N-glycosylation conditions. Copyright

Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol

Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath ≥ 105 °C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.