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• Solvents and Organic Chemicals Organic Compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleosides Pyrimidine nucleosides
• Solvents and Organic Chemicals Organic Compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleosides

Recent Advances in the Application of 5'-O-tert-Butyldimethylsilyluridine (CAS: 54925-65-4) in Chemical Biology and Pharmaceutical Research

The compound 5'-O-tert-Butyldimethylsilyluridine (CAS: 54925-65-4) has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This uridine derivative, protected by a tert-butyldimethylsilyl (TBDMS) group at the 5'-hydroxyl position, serves as a crucial intermediate in the synthesis of modified nucleosides, oligonucleotides, and other biologically active molecules. Its unique chemical properties make it an invaluable tool for researchers exploring nucleic acid chemistry, antiviral drug development, and targeted therapeutics.

Recent studies have highlighted the role of 5'-O-tert-Butyldimethylsilyluridine in the synthesis of antisense oligonucleotides (ASOs) and small interfering RNAs (siRNAs). The TBDMS protecting group enhances the stability of the uridine moiety during solid-phase synthesis, allowing for the efficient production of high-purity oligonucleotides. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that the use of this protected uridine derivative significantly improved the yield and purity of siRNA constructs targeting viral RNA, paving the way for more effective antiviral therapies.

In addition to its applications in oligonucleotide synthesis, 5'-O-tert-Butyldimethylsilyluridine has been employed in the development of novel nucleoside analogs with potential anticancer activity. Researchers at the Scripps Research Institute recently reported the synthesis of a series of uridine derivatives using 54925-65-4 as a key starting material. These analogs exhibited selective cytotoxicity against cancer cell lines while showing minimal effects on normal cells, suggesting their potential as targeted anticancer agents. The study, published in ACS Chemical Biology, emphasized the importance of the TBDMS group in controlling the regioselectivity of subsequent chemical modifications.

The compound has also found applications in metabolic labeling studies of RNA. A groundbreaking technique described in Nature Methods (2024) utilized 5'-O-tert-Butyldimethylsilyluridine as a precursor for the synthesis of bioorthogonal uridine analogs. These analogs enabled real-time tracking of RNA synthesis and turnover in living cells, providing unprecedented insights into cellular RNA dynamics. The TBDMS protection was critical for the successful incorporation of click chemistry handles while maintaining the biological activity of the resulting nucleosides.

From a pharmaceutical perspective, the stability and solubility properties imparted by the TBDMS group make 54925-65-4 particularly valuable for prodrug development. Several recent patent applications have disclosed uridine-based prodrugs derived from this protected nucleoside, designed to improve oral bioavailability and tissue targeting. These developments highlight the growing importance of 5'-O-tert-Butyldimethylsilyluridine in addressing formulation challenges associated with nucleoside-based therapeutics.

Looking forward, researchers anticipate expanded applications of 5'-O-tert-Butyldimethylsilyluridine in emerging fields such as RNA nanotechnology and mRNA vaccine development. Its ability to serve as a versatile building block for RNA modification, coupled with its favorable chemical properties, positions this compound as a key player in the next generation of nucleic acid-based therapeutics. Ongoing research aims to further optimize its synthetic utility and explore novel biological activities of its derivatives.

• 245078-05-1(1-(2'-O-allyl-3'-O-(tert-butyldiMethylsilyl)-beta-D-arabinofuranosyl)uracil)
• 69504-11-6(URIDINE, 3'-O-[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]-)
• 922508-26-7(2'-TBDMS-5-Me-rU)
• 119794-52-4(5'-O-[(1,1-Dimethylethyl)dimethylsilyl]-5-methyluridine)
• 54925-68-7(1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-2-yl]pyrimidine-2,4-dione)
• 64911-18-8(3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine)
• 54925-71-2(2'-O-tert-Butyldimethylsilyluridine)
• 76223-05-7(Uridine, 2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-)
• 141208-18-6(Uridine, 3'-deoxy-5'-O-[(1,1-dimethylethyl)dimethylsilyl]-)
• 139888-00-9(Uridine,2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-4'-(hydroxymethyl)-)