N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine
[CAS# 251647-48-0]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)adenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-(2-methoxyethoxy)oxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₄₁H₄₁N₅O₈
• Molecular Weight: 731.79
• CAS Registry Number: 251647-48-0
• SMILES: COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC)O

Properties

• Density: 1.31

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H320-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-(2-methoxyethyl)adenosine, commonly abbreviated as N-Benzoyl-5'-O-[bis(4-MeO-Ph)PhMe]-2'-O-(2-MeOEt)Ado, is a complex nucleoside derivative designed to improve stability and functionality in biochemical research and therapeutic applications. The compound combines multiple modifications to optimize its properties.

N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-(2-methoxyethyl)adenosine was developed to address the limitations of standard adenosine in terms of stability and reactivity. Enhanced chemical stability and solubility are achieved by introducing a benzoyl group at the nitrogen position, a bis(4-methoxyphenyl)benzyl group at the 5' position, and a 2'-O-(2-methoxyethyl) modification.

In RNA and DNA research, this modified adenosine is valuable for its improved stability. The 2'-O-(2-methoxyethyl) group protects the nucleoside from degradation by ribonucleases and deoxyribonucleases, making it a useful component for building stable RNA and DNA molecules. Its resistance to hydrolysis and enzymatic attack facilitates more accurate studies of nucleic acid structure and function.

N-Benzoyl-5'-O-[bis(4-methoxyphenyl)benzyl]-2'-O-(2-methoxyethyl)adenosine is used in nucleic acid synthesis to produce robust oligonucleotides with improved performance characteristics. The stability of this compound ensures that the synthesized nucleotide maintains its integrity during the synthesis process and in subsequent applications, including gene expression analysis and therapeutic nucleic acids.

In therapeutic development, this nucleoside derivative shows potential for creating more effective antiviral and anticancer agents. The combination of chemical modifications enhances its pharmacokinetic properties, resulting in improved drug stability and longer-lasting effects. Researchers could use this modified adenosine to design nucleoside analogs with improved therapeutic properties, potentially reducing dosing frequency and improving efficacy.

References

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