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Usage

Uses

Used in RNA Synthesis:
3',5'-TIPS-5-Me-Uridine is used as a building block in the synthesis of RNA molecules for enhancing their stability and binding affinity. The chemical modification allows for the creation of RNA structures with improved properties, which can be crucial for various applications.
Used in Research:
3',5'-TIPS-5-Me-Uridine is used as a research tool for studying the structure and function of RNA. Its unique properties make it an ideal candidate for probing the mechanisms of RNA folding, stability, and interactions with other molecules.
Used in Drug Development:
In the pharmaceutical industry, 3',5'-TIPS-5-Me-Uridine is utilized in the development of nucleic acid-based therapeutics. Its protective tris(trimethylsilyl) group and the ability to enhance RNA stability make it a promising component in the design of drugs targeting RNA-related diseases.
Used in Diagnostics:
3',5'-TIPS-5-Me-Uridine is also employed in the development of RNA-based diagnostic tools. Its enhanced stability and resistance to degradation can improve the performance and reliability of diagnostic assays that rely on the detection or manipulation of RNA molecules.

Upstream product

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

Downstream Products

• 183281-81-4 1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]thymine 
• 1054489-35-8 C₂₉H₄₃BrN₂O₈Si₂ 
• 1414853-71-6 N³-Boc-3',5'-O-1,1,3,3-tetraisopropyl-1,3-disiloxane-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1414853-72-7 N³-Boc-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1414853-76-1 N³-Boc-3',5'-O-bis-benzoyl-2'-O-methylsulfonyloxy-5-methyluridine 
• 1414853-79-4 N³-Boc-3',5'-O-bis-tetrahydropyranyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1414853-81-8 N³-Boc-3',5'-O-bis-methoxymethyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1414853-83-0 N³-Boc-3',5'-O-bis-benzoyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine 
• 1350852-18-4 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-O-(2,6-dimethylphenyl)-5-methyluridine 
• 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 

Relevant academic research and scientific papers

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

Synthesis and in vitro growth inhibitory activity of novel silyl- and trityl-modified nucleosides

Seventeen silyl- and trityl-modified (5′-O- and 3′,5′-di-O-) nucleosides were synthesized with the aim of investigating the in vitro antiproliferative activities of these nucleoside derivatives. A subset of the compounds was evaluated at a fixed concentra

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

Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties

In this study, it was found that the arrangement of consecutive thiocarbonyl groups of s2T and m5s2C remarkably stabilized the pre-protonated form of the triplex, and that the stabilization of the pre-protonated form increased the pKa value of a cytosine derivative in the triplex.

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

An azidomethyl protective group in the synthesis of oligoribonucleotides by the phosphotriester method

A rapid and effective method of an automatic oligoribonucleotide synthesis alternative to the phosphoramidite one was developed. This method is based on the phosphotriester approach to internucleotide bond formation under intramolecular O-nucleophilic cat

NUCLEOSIDE BASED PROLIFERATION IMAGING MARKERS

Disclosed herein are novel radiolabeled nucleosides and methods for detecting cellular proliferation in a mammal, the method comprising administrating an effective amount of a radiolabeled nucleoside; the method comprising: a) administering to the mammal a diagnostically effective amount of the nucleoside to the mammal; b) allowing the nucleoside to distribute into the effective tissue; and c) imaging the tissue, wherein an increase in binding of the compound to tissue compared to a normal control level of binding indicates that the mammal is suffering from a disease involving cellular proliferation.

Preparation of deoxynucleosides

Methods for preparing deoxynucleosides from their corresponding ribonucleosides by forming 3-tert-butylphenoxythiocarbonylderivatives of the ribonucleosides and subsequently effecting radical deoxygenation reactions at the carbon atoms to be deoxygenated.

Nucleotides. Part XLII. The 2-dansylethoxycarbonyl (=2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl]}ethoxycarbonyl; Dnseoc) group for protection of the 5'-hydroxy function in oligoribonucleotide synthesis

The 2-dansylethoxycarbonyl (Dnseoc) group was employed for protection of the 5'-hydroxy function in oligoribonucleotide synthesis by the phosphoramidite approach using the acid-labile tetrahydro-4-methoxy-2H-pyran-4-yl (Thmp) group for 2'-protection. The

Nucleosides and nucleotides. 97. Synthesis of new broad spectrum antineoplastic nucleosides, 2'-deoxy-2'-methylidenecytidine (DMDC) and its derivatives

A new type of antineoplastic nucleoside, 2'-deoxy-2'-methylidenecytidine (DMDC) has been synthesized from the corresponding 2'-keto pyrimidine nucleosides 3 and 8 by the Wittig reaction. During the course of the reaction, we found that an intermediate bet