2'-O-tert-Butyldimethylsilyluridine
[CAS# 54925-71-2]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-tert-Butyldimethylsilyluridine
• Synonyms: 1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• Molecular Formula: C₁₅H₂₆N₂O₆Si
• Molecular Weight: 358.46
• CAS Registry Number: 54925-71-2
• SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O

Properties

• Solubility: Very slightly soluble (0.15 g/L) (25 °C), Calc.^*
• Density: 1.25±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 192-194 °C (ethyl acetate hexane )^**

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

^** Hwu, Jih Ru

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

2'-O-tert-Butyldimethylsilyluridine (2'-O-TBS-uridine) is an important nucleoside derivative in the field of chemical and biological research. The compound features a tert-butyldimethylsilyl (TBS) protecting group at the 2' position of the ribose sugar, which is crucial in nucleoside chemistry due to its stability and reactivity.

The development of 2'-O-TBS-uridine stems from the need for stable, protectable nucleoside derivatives that can withstand a variety of chemical reactions and conditions. Researchers aimed to create a nucleoside with enhanced stability and ease of handling during synthesis, especially in the presence of reactive groups or under harsh conditions. The introduction of the TBS group provides a powerful solution, providing a stable and easily removable protecting group.

The synthesis of 2'-O-TBS-uridine involves the selective protection of uridine with a TBS group. This modification is essential to prevent unwanted reactions at the 2' position during chemical transformations. The compound was first synthesized and reported in the early 2000s, demonstrating its potential in nucleoside chemistry and related fields.

2'-O-TBS-uridine is widely used as an intermediate in the synthesis of various nucleoside analogs. The TBS group provides significant protection, allowing complex modifications to the nucleoside structure without degradation. This stability is essential for the development of novel nucleoside derivatives with potential pharmaceutical and biotechnological applications.

In RNA chemistry, 2'-O-TBS-uridine is used to produce modified RNA molecules. TBS protection allows the synthesis of RNA sequences that are resistant to degradation and more stable during manipulation. This property is particularly valuable for the creation of therapeutic RNA molecules, including antisense oligonucleotides and RNA interfering agents.

The compound plays an important role in the pharmaceutical industry as a precursor for nucleoside drugs. The stability conferred by the TBS group enhances the efficacy of nucleoside analogs used in antiviral and anticancer treatments. Researchers have used 2'-O-TBS-uridine to develop drugs with improved pharmacokinetic properties and reduced side effects.

References

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