2'-O-(tert-Butyldimethylsilyl)-N-isobutyrylguanosine
[CAS# 182007-86-9]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-(tert-Butyldimethylsilyl)-N-isobutyrylguanosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• Molecular Formula: C₂₀H₃₃N₅O₆Si
• Molecular Weight: 467.59
• CAS Registry Number: 182007-86-9
• SMILES: CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O[Si](C)(C)C(C)(C)C

Properties

• Solubility: Practically insoluble (0.02 g/L) (25 ºC), Calc.^*
• Density: 1.37±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.612, 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
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

2'-O-(tert-butyldimethylsilyl)-N-isobutyrylguanosine, abbreviated 2'-O-(TBDMS)-N-IBG, is a complex nucleoside derivative with enhanced stability and potential for a variety of applications. The compound embodies advances in nucleoside chemistry aimed at improving the manipulation and functionality of guanosine analogs.

The development of 2'-O-(TBDMS)-N-IBG was driven by the need for more robust nucleoside analogs that maintain structural integrity under a variety of conditions. By introducing a tert-butyldimethylsilyl (TBDMS) group at the 2' position of the ribose sugar, the researchers aimed to protect the nucleoside from hydrolysis and oxidation, which can limit the utility of unmodified nucleosides in practical applications.

The synthesis of the compound involves attaching a TBDMS protecting group to the 2'-hydroxyl group of guanosine, followed by the introduction of an isobutyryl group at the N position of the guanine base. These modifications enhance the nucleoside's stability and resistance to chemical degradation, making it suitable for a variety of research and therapeutic purposes.

2'-O-(TBDMS)-N-IBG is valuable in nucleic acid research due to its increased stability. The TBDMS group protects nucleosides from premature degradation during synthesis and handling, allowing for more accurate studies of nucleic acid interactions and properties. Researchers have used this modified guanosine to study RNA structure, function, and stability, providing insights into mechanisms of gene expression and regulation.

In drug development, 2'-O-(TBDMS)-N-IBG serves as a model for the design of new guanosine-based drugs with improved stability and efficacy. Isobutyryl and TBDMS protection can be used to tailor the pharmacokinetic properties of nucleoside analogs, leading to the development of drugs with improved bioavailability and therapeutic potential. The stability of this compound makes it a candidate for further development as an antiviral and anticancer therapeutic.

The stability of this compound also makes it a useful intermediate in chemical synthesis. The TBDMS group can be selectively removed in a controlled manner, allowing for precise modification of nucleosides in complex chemical syntheses. This capability is important in the development of novel nucleoside analogs and other bioactive molecules.