70230-70-5

Basic information

• Product Name: Adenosine, N,N-dimethyl-, 2',3',5'-tribenzoate
• CAS NO: 70230-70-5
• Molecular Formula: C33H29N5O7
• Molecular Weight: 607.623
• Mol File: 70230-70-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Adenosine, N,N-dimethyl-, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, N,N-dimethyl-, 2',3',5'-tribenzoate(70230-70-5)
• EPA Substance Registry System: Adenosine, N,N-dimethyl-, 2',3',5'-tribenzoate(70230-70-5)

Safety Data

• Hazardous Substances Data: 70230-70-5(Hazardous Substances Data)

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 938-55-6 6-Dimethylaminopurine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 98-88-4 benzoyl chloride 
• 2620-62-4 N,N-dimethyladenosine 
• 3510-73-4 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 16645-06-0 N,N-dimethylhydroxylamine hydrochloride 

Downstream Products

• 71118-18-8 C₃₃H₂₇N₅O₈ 
• 6741-88-4 2',3',5'-tri-O-benzoylinosine 
• 2620-62-4 N,N-dimethyladenosine 
• 70230-71-6 2',3',5'-tri-O-benzoyl-N,N,3-trimethyladenosine iodide 

Relevant articles and documents

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.

Synthesis of 5-(Methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide, a Synthetic Intermediate for 3-Methyl-9-β-D-ribofuranosylpurines

Treatment of 2',3',5'-tri-O-benzoyl-N,N-dimethyladenosine (2c) with methyl iodide in AcNMe2 gave the 3-methyl derivative (3c) as a sole product.Alkaline hydrolysis of 3c afforded the title imidazolecarboxamide (4a), whose hydroxy groups were acetylated selectively with Ac2O-pyridine.Similar methylation of 2',3',5'-tri-O-benzyl-N,N-dimethyladenosine (2d) followed by alkaline hydrolysis provided 2',3',5'-tri-O-benzyl-4a (4d) in good yield.