7791-71-1

Usage

Uses

Used in Molecular Biology and Medicinal Chemistry:
5'-O-Tritylthymidine is used as a key building block for the production of nucleic acid analogues, which are vital in genetic research and the development of antiviral and anticancer drugs. Its trityl protecting group allows for the controlled synthesis of complex nucleotide structures, enhancing the efficiency and specificity of these analogues.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 5'-O-Tritylthymidine is used as a precursor for the synthesis of nucleotide analogues that have potential applications in antiviral and anticancer therapies. The protecting group ensures that the nucleotide analogues can be synthesized with high purity and specificity, improving their therapeutic efficacy and reducing side effects.
Used in Research and Development:
5'-O-Tritylthymidine is employed as a research tool in the study of nucleic acid structure and function. Its ability to protect the 5'-hydroxyl group during synthesis allows researchers to explore the properties and interactions of nucleotides and their analogues, contributing to a deeper understanding of genetic processes and the development of novel therapeutic agents.
Used in Synthesis of Nucleoside and Nucleotide Derivatives:
In the synthesis of nucleoside and nucleotide derivatives, 5'-O-Tritylthymidine is used as a versatile intermediate. The trityl group provides a stable and easily removable protecting group, facilitating the synthesis of a wide range of nucleotide analogues with diverse chemical and biological properties.
Used in Drug Design and Discovery:
5'-O-Tritylthymidine is utilized in drug design and discovery as a starting material for the development of novel therapeutic agents. Its role in the synthesis of nucleotide analogues with antiviral and anticancer properties makes it an essential component in the search for new and effective treatments for various diseases.

Upstream product

• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 65475-49-2 1-(5-O-trityl-β-D-glycero-pentofuran-3-ulosyl)thymine 
• 50-89-5 thymidine 
• 20290-92-0 1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine 
• 87-72-9 L-(+)-arabinose 
• 3795-68-4 methyl α-L-arabinofuranoside 
• 76-83-5 trityl chloride 
• 16033-24-2 1-<α-L-Arabinofuranosyl>thymine 
• 137174-38-0 5-methyl-1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 
• 42793-97-5 2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose 
• 131682-41-2 1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 
• 16053-52-4 threothymidine 
• 22423-25-2 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine 
• 135182-37-5 3'-O-TCBOC-5'-O-tritylthymidin 

Downstream Products

• 130457-20-4 C₄₄H₄₈N₅O₁₃PS 
• 99680-09-8 C₄₇H₄₆ClN₄O₁₃P 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 78550-81-9 C₃₆H₃₈Cl₂N₄O₁₇P₂ 
• 78710-08-4 C₄₇H₄₆ClN₄O₁₃P 
• 143331-48-0 ((S)-2-Methyl-butyl)-phosphonic acid bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 99680-14-5 Phosphoric acid 2-chloro-phenyl ester bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 91326-88-4 Benzoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{methyl-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-phosphinoyloxymethyl}-tetrahydro-furan-3-yl ester 
• 83831-80-5 Methyl-phosphonic acid bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 141089-63-6 Acetic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxysulfonyl]-ethyl}-tetrahydro-furan-3-yl ester 
• 141089-62-5 2-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 107036-53-3 3'-O-(1-imidazolylthiocarbonyl)-5'-O-tritylthymidine 
• 83479-97-4 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Hydrogen-bonding linkage of thymidine derivatives with carboxylic acid and pyridyl groups in a crystalline state

Thymidine derivatives with carboxylic acid and pyridyl groups were synthesized for constructing one-dimensional network structure based on hydrogen bonding in crystalline state. The solid sate structures and hydrogen bonding networks of the thymidine derivatives were characterized by single X-ray diffraction analysis. The thymidine derivatives formed a zwitterion structure with a pyridinium proton and a carboxylate moiety in a crystalline state due to transfer of a proton from the carboxylic acid to the pyridyl moiety. Strong hydrogen bonds between the pyridinium proton and the carboxylate moiety connected the thymidine units, resulting in a one-dimensional polymeric structure with a uniform direction reminiscent of the structure of single-strand polythymidine. The chemical structure of the pyridyl group affects the hydrogen-bonding networks. The well-designed hydrogen-bonding interaction served as connecting parts for polythymidine mimics even in the presence of other hydrogen-bonding motifs such as nucleobases. Copyright

The cleavage of the 2,2,2-trichloro-1,1-dimethylethoxycarbonyl protective group by tin(II) tris(benzenethiolate)

The cleavage of the 2,2,2-trichloro-1,1-dimethylethoxycarbonyl (trichloro-tert-butoxycarbonyl, TCBOC) protective group for amino and hydroxy functions by tin(II) tris[benzenethiolate] in the presence of tetrabutylammonium cobalt(II) phthalocyanine-5,12,19,26-tetrasulfonate is reported. This combination is superior to previously used deblocking reagents for the TCBOC-group.

Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose

An original and efficient stereocontrolled synthesis of ribonucleosidic homo- and heterodimers has been achieved from inexpensive d-xylose. This successful strategy involved the sequential introduction of nucleobases, using two stereocontrolled N-glycosidation reactions, from a common two-furanoside amide-linked scaffold offering the possibility of obtaining any given base sequence. The pertinence of this approach is illustrated through the preparation of the homodimers UU-34 and TT-35 in 18 steps with an excellent overall yield of more than 10% from d-xylose, while the heterodimer route led to UT-39 in 19 steps with around 10% overall yield.

Anti-flavivirus Activity of Different Tritylated Pyrimidine and Purine Nucleoside Analogues

A series of tritylated and dimethoxytritylated analogues of selected pyrimidine and purine nucleosides were synthesized and evaluated for their in vitro inhibitory activity against two important members of the genus Flavivirus in the Flaviviridae family, the yellow fever (YFV) and dengue viruses (DENV). Among all compounds tested, the 5′-O-tritylated and the 5′-O-dimethoxytritylated 5-fluorouridine derivatives exerted potency against YFV. Interestingly in the series of purine analogues, the 5′O, N-bis-tritylated fludarabine derivative revealed strong inhibitory activity against DENV at μm concentrations, however significantly weaker potency against YFV.

Optimized synthesis of 3′-O-aminothymidine and evaluation of its oxime derivative as an anti-HIV agent

The synthesis and isolation of 3′-O-aminothymidine oximes have been optimized. Synthesized compounds were characterized by NMR and UV spectral and analytical data. A mixture of previously not reported syn and anti isomers of acetaldoximes was assessed for anti-HIV activity and the prevention of syncytia formation caused by HIV-1 infection.

In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues

Several flaviviruses, such as the yellow fever virus and the dengue virus cause severe and potentially lethal infection in man. Following up on our initial hit 3′,5′-bistritylated uridine 1, a series of alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against dengue fever virus and yellow fever virus. Hereto, alkyl and aryl groups were attached at various positions of the sugar ring combined with subtle variation of the heterocyclic base. Among the new series of derivatives, 3′,5′-di-O-trityl-5-fluoro-2′-deoxyuridine (39) was the most efficient in this series and inhibited both yellow fever virus and dengue virus replication with a 50% effective concentration (EC50) of ～1 μg/mL without considerable cytotoxicity. The other fluorinated derivatives proved more toxic. Almost all diphenylmethylated pyrimidine nucleosides with 3′,5′-di-O-benzhydryl-2′-deoxyuridine (50) as the example were endowed with strong cytotoxic effects down to 1 μg/mL.

In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues

Following up on a hit that was identified in a large scale cell-based antiviral screening effort, a series of triphenylmethyl alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against the dengue virus (DENV) and the yellow fever virus (YFV). Hereto, trityl moieties were attached at various positions of the sugar ring combined with subtle variations of the heterocyclic base. Several triphenylmethyl modified nucleosides were uncovered being endowed with submicromolar in vitro antiviral activity against the YFV. The most selective inhibitor in this series was 3′,5′-bis-O-tritylated-5-chlorouridine (1b) affording a selectivity index of over 90, whereas the 3′,5′-bis-O-tritylated inosine congener (5b) displayed the highest activity, but proved more toxic. The finding of these lipophilic structures being endowed with high antiviral activity for flaviviruses, should stimulate the interest for further structureeactivity research.

Synthesis of new pyrimidine nucleoside derivatives with nitric oxide donors for antiviral activity

New pyrimidine nucleoside derivatives with nitric oxide (NO) donor were systematically synthesized. The antivirus activities of these nucleoside analogues against vesicular stomatitis virus (VSV) in Wish cell were evaluated. It was demonstrated that most of compounds had stronger antiviral acitivity than acyclovir, while their toxicities were similar or lower to acyclovir.

Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide-alkyne 1,3-dipolar cycloaddition

An efficient, catalyst free, 1,3-dipolar cycloaddition strategy to conjugate nucleosides and nucleotides with isoxazoles under atmospheric conditions and in an aqueous environment is reported. The protocol involves chloramine-T as a practical reagent to induce in situ nitrile oxide formation and the alkyne partner is attached to the sugar residue or the nucleobase. The reactions are regiospecific, fast and high yielding.

3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis

Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2′- or 3′-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3′-bromo-3′-deoxy- arabinofuranosylthymine (33) was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC 50 = 1 μg/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 μg/mL). Compound 33 also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 μg/mL concentration) than extracellular mycobacteria (75% reduction at 10 μg/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 μg/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.