N-Acetyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine
[CAS# 401812-97-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: N-Acetyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine
• Synonyms: N-[1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• Molecular Formula: C₁₇H₂₉N₃O₆Si
• Molecular Weight: 399.51
• CAS Registry Number: 401812-97-3
• SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O[Si](C)(C)C(C)(C)C

Properties

• Solubility: Very slightly soluble (0.15 g/L) (25 ºC), Calc.^*
• Density: 1.28±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

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

Discovory and Applicatios

N-acetyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine has a 2'-O-(tert-butyldimethylsilyl) group, which is a commonly used protecting group in organic synthesis. This protecting group has excellent stability and can be selectively removed under mild conditions. Its acetylation further enhances the stability and solubility of the nucleoside derivative, making it an attractive candidate for various synthetic applications.

The main application of N-acetyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine is in nucleoside chemistry, where it is a key intermediate in the synthesis of more complex nucleoside analogs. The stability provided by the silicon and acetyl groups allows chemists to perform a wide range of transformations without significant degradation of the nucleoside. This property is particularly useful in the synthesis of nucleoside drugs and other biologically active compounds.

In the pharmaceutical industry, this compound is used to develop nucleoside analogs with potential therapeutic applications. For example, it can be used to make modified nucleosides with increased efficacy or reduced toxicity compared to natural nucleosides. These modified nucleosides can then be tested for their potential as antiviral or anticancer agents.

N-acetyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine is also valuable in molecular biology research. It can be used to synthesize labeled nucleotides or prepare oligonucleotides for a variety of applications, including gene synthesis and nucleic acid sequencing. The stability of the protecting group ensures that the nucleotide remains intact throughout the synthesis and subsequent analysis.