130983-87-8

Basic information

• Product Name: 3',5'-TIPS-5-Me-Uridine
• Synonyms: 3',5'-TIPS-5-Me-Uridine;3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)-5-methyluridine
• CAS NO: 130983-87-8
• Molecular Formula: C₂₂H₄₀N₂O₇Si₂
• Molecular Weight: 500.73
• Mol File: 130983-87-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• PKA: 9.48±0.10(Predicted)
• CAS DataBase Reference: 3',5'-TIPS-5-Me-Uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-TIPS-5-Me-Uridine(130983-87-8)
• EPA Substance Registry System: 3',5'-TIPS-5-Me-Uridine(130983-87-8)

Safety Data

• Hazardous Substances Data: 130983-87-8(Hazardous Substances Data)

Usage

General Description

3',5'-TIPS-5-Me-Uridine is a modified uridine nucleoside containing a 5'-O-tris(trimethylsilyl) group and a methyl group at the 5-position of the pyrimidine ring. This chemical modification is commonly used in the synthesis of RNA molecules, where it can enhance the stability and binding affinity of the nucleic acid. Additionally, 3',5'-TIPS-5-Me-Uridine is utilized as a research tool in studies of RNA structure and function, as well as in the development of therapeutic nucleic acid-based drugs. The presence of the tris(trimethylsilyl) group also offers protection against nucleolytic degradation, making it a valuable component in the design of RNA-based therapeutics or diagnostics.

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 1463-10-1 5-Methyluridine 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 

Downstream Products

• 1054489-35-8 C₂₉H₄₃BrN₂O₈Si₂ 
• 1350852-18-4 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-O-(2,6-dimethylphenyl)-5-methyluridine 
• 1350852-19-5 C₃₁H₅₀N₂O₇Si₂ 
• 1350852-20-8 C₃₁H₅₀N₂O₆SSi₂ 
• 1350852-21-9 C₃₂H₃₄N₂O₇S 
• 1350852-12-8 C₄₁H₅₁N₄O₈PS 
• 1350852-22-0 C₄₁H₅₂N₅O₇PS 
• 1054489-48-3 2-(3-((2R,3R,4R,5R)-3,4-bis(tert-butoxycarbonyloxy)-5-((tert-butoxycarbonyloxy)methyl)tetrahydrofuran-2-yl)-5-methyl-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)ethyl 4-methylbenzenesulfonate 
• 1054489-46-1 C₃₄H₄₈N₂O₁₃ 
• 1054489-41-6 C₂₆H₂₇BrN₂O₈ 
• 1054489-98-3 C₁₉H₂₀BrFN₂O₇ 
• 1054489-43-8 C₁₉H₂₄N₂O₇ 
• 1414853-83-0 N³-Boc-3',5'-O-bis-benzoyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1414853-81-8 N³-Boc-3',5'-O-bis-methoxymethyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine 

Relevant articles and documents

A novel method for stereospecific fluorination at the 2′-arabino- position of pyrimidine nucleoside: Synthesis of [18F]-FMAU

Direct fluorination of a pyrimidine nucleoside at the 2′-arabino- position has been deemed to be extremely difficult, if not impossible. The conventional synthesis of 2′-deoxy-2′-fluoro-5-methy-1-β-D- arabinofuranosyluracil (FMAU) and its 5-substituted analogs involves stereospecific fluorination of the 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2- sulfonate ester followed by bromination at the C1-postion, and then coupling with pyrimidine-bis-trimethylsilyl ether. Several radiolabeled nucleoside analogs, including [18F]FMAU, and other 5-substituted analogs, were developed according to this methodology. However, routine production of these compounds using this multi-step process is inconvenient and limits their clinical application. We developed a novel precursor and method for direct fluorination of preformed nucleoside analogs at the 2′-arabino position, exemplified via radiosynthesis of [18F]FMAU. The 2′-methylsulfonyl-3′,5′-O-tetrahydropyranyl-N 3-Boc-5-methyl-1-β-D-ribofuranosiluracil was synthesized in multiple steps. Radiofluorination of this precursor with K18F/ kryptofix produced 2′-deoxy-2′-[18F]fluoro-3′, 5′-O-tetrahydropyranyl-N3-Boc-5-methyl-1-β-D- arabinofuranosiluracil. Acid hydrolysis followed by high-performance liquid chromatography purification produced the desired [18F]FMAU. The average radiochemical yield was 2.0% (decay corrected, n=6), from the end of bombardment. Radiochemical purity was >99%, and specific activity was >1800 mCi/μmol. Synthesis time was 95-100 min from the end of bombardment. This direct fluorination is a novel method for synthesis of [ 18F]FMAU, and the method should be suitable for production of other 5-substituted pyrimidine analogs, including [18F]FEAU, [ 18F]FIAU, [18F]FFAU, [18F]FCAU, and [ 18F]FBAU. Copyright

An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside: Radiosynthesis of 2′-deoxy-2′- [18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil

Direct fluorination at the 2′-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [ 18F]FMAU, albeit in low yields. H

METHOD FOR INTRODUCING NUCLEIC-ACID-PROTECTING GROUP

It is an object of the invention to provide a simple and economical method for introducing the following substituent (I) at the 2'-hydroxyl group of the ribose of a ribonucleic acid derivative whose 3'-hydroxyl group and 5'-hydroxyl group are protected wi