N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine
[CAS# 69504-07-0]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₂₃H₃₁N₅O₅Si
• Molecular Weight: 485.61
• CAS Registry Number: 69504-07-0
• SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)O

Properties

• Solubility: Insoluble (4.7E^-4 g/L) (25 ºC), Calc.^*
• Density: 1.33±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine is an important nucleoside derivative in the field of nucleic acid chemistry. The compound is characterized by benzoylation at the N6 position and silylation at the 2'-O position, which has enhanced stability and unique chemical properties, which are beneficial for various applications in molecular biology and medicinal chemistry.

The discovery of N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine is part of a broad effort to develop modified nucleosides with improved properties for use in chemical synthesis and therapeutic applications. Researchers aim to create nucleoside derivatives that are more stable and more versatile than natural nucleosides. The combination of the N6-benzoyl group and the 2'-O-tert-butyldimethylsilyl (TBDMS) group produces a compound with enhanced nuclease resistance and increased hydrophobicity, making it suitable for a variety of advanced applications.

N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine is widely used in the synthesis of RNA molecules. The TBDMS group at the 2'-O position protects the nucleoside from unwanted side reactions and degradation during the chemical synthesis of RNA oligonucleotides. This protection is essential for creating high-fidelity RNA sequences, which are critical for a variety of research and therapeutic applications, including mRNA vaccines and RNA-based drugs.

In chemical biology, this compound is a valuable tool for studying nucleic acid interactions and functions. Benzoyl and TBDMS modifications can be used to create stable RNA and DNA probes for studying molecular mechanisms and interactions within cells. These probes aid in the understanding of genetic regulation, RNA processing, and protein-nucleic acid interactions, providing insights into fundamental biological processes.

N6-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine is also used to develop nucleoside analog drugs. These modifications enhance the stability and bioavailability of these analogs, making them more effective against viral infections and cancer. By incorporating into viral or cancerous DNA/RNA, these modified nucleosides can disrupt the replication process, providing potential therapeutic benefits.

This compound plays a key role in the design of therapeutic oligonucleotides, including antisense oligonucleotides and small interfering RNA (siRNA). The enhanced stability provided by TBDMS and benzoyl groups improves the efficacy of these oligonucleotides in targeting specific RNA sequences for gene silencing or regulation. This has important implications for treating genetic diseases and disorders caused by abnormal gene expression.