7791-71-1

Basic information

• Product Name: 5'-O-Tritylthymidine
• Synonyms: 5''-O-TRITYLTHYMIDINE(5-OTT);5-Methyl-5'-O-trityl-2'-deoxyuridine;5'-O-Triphenylmethylthymidine;Thymidine, 5'-o-(triphenylmethyl)-;Trt-dT;5’-o-(triphenylmethyl)-thymidin;5'-O-TRITYLTHYMIDINE;1-((2R,4S,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS NO: 7791-71-1
• Molecular Formula: C₂₉H₂₈N₂O₅
• Molecular Weight: 484.54
• EINECS: 2017-001-1
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 7791-71-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 125 °C(Solv: acetone (67-64-1); ethyl ether (60-29-7))
• Appearance: /
• Density: 1.275g/cm³
• Storage Temp.: −20°C
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 5'-O-Tritylthymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-Tritylthymidine(7791-71-1)
• EPA Substance Registry System: 5'-O-Tritylthymidine(7791-71-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7791-71-1(Hazardous Substances Data)

Usage

General Description

5'-O-Tritylthymidine is a chemical compound that is commonly used in the synthesis of nucleosides and nucleotides. It is a derivative of thymidine, a nucleoside found in DNA, and is used as a precursor in the production of various nucleotide analogues for research and pharmaceutical purposes. The trityl protecting group attached to the 5'-hydroxyl group of thymidine prevents unwanted reactions during the synthesis process, allowing for the controlled modification of the molecule. 5'-O-Tritylthymidine is a key building block in the production of nucleic acid analogues, which are important in the study of genetics and in the development of antiviral and anticancer drugs. Due to its versatility and importance in nucleotide synthesis, 5'-O-Tritylthymidine is a widely used chemical in the field of molecular biology and medicinal chemistry.

Upstream product

• 76-83-5 trityl chloride 
• 50-89-5 thymidine 
• 79258-32-5 3'-O-(2-hydroxy)ethoxycarbonyl-5'-O-tritylthymidine 
• 135182-37-5 3'-O-TCBOC-5'-O-tritylthymidin 
• 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 
• 22423-25-2 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine 
• 16053-52-4 threothymidine 
• 131682-41-2 1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 
• 20290-92-0 1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine 
• 87-72-9 L-(+)-arabinose 
• 42793-97-5 2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose 
• 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 
• 137146-99-7 1-<3',5'-O-(1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranosyl>thymine 

Downstream Products

• 4305-48-0 thymidylyl-(5'->3')-O^5'-trityl-thymidine 
• 16562-50-8 thymidine 3'-O-(4-nitrophenyl)phosphate 
• 23583-46-2 3'-O-acetyl-5'-O-triphenylmethylthymidine 
• 63593-01-1 3'-O-benzyl-2'-deoxythymidine 
• 141690-73-5 3'-Tosyl-5'-O-trityl thymidine 
• 108480-33-7 2'-deoxy-[5']adenylic acid-(O^5'-trityl-thymidin-3'-yl ester) 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 72718-44-6 Acetic acid (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-{[(2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester 
• 130457-20-4 C₄₄H₄₈N₅O₁₃PS 
• 99680-09-8 C₄₇H₄₆ClN₄O₁₃P 
• 137147-01-4 3'-O-Methylsulfonyl-5'-O-triphenylmethyl-α-L-thymidine 
• 143331-47-9 Benzyl-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 
• 91304-85-7 C₃₆H₃₄N₅O₅P 
• 26886-08-8 [3']thymidylic acid mono-(4-nitro-phenyl ester); ammonium salt 

Relevant articles and documents

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

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.

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.