42214-24-4

Basic information

• Product Name: 5'-O-TRITYL-3'-O-MESYLTHYMIDINE
• Synonyms: 5'-O-TRITYL-3'-O-MESYLTHYMIDINE
• CAS NO: 42214-24-4
• Molecular Formula: C₃₀H₃₀N₂O₇S
• Molecular Weight: 562.6334
• Mol File: 42214-24-4.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.38g/cm³
• Refractive Index: 1.654
• Storage Temp.: -20°C
• CAS DataBase Reference: 5'-O-TRITYL-3'-O-MESYLTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-TRITYL-3'-O-MESYLTHYMIDINE(42214-24-4)
• EPA Substance Registry System: 5'-O-TRITYL-3'-O-MESYLTHYMIDINE(42214-24-4)

Safety Data

• Hazardous Substances Data: 42214-24-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5'-O-TRITYL-3'-O-MESYLTHYMIDINE is used as a protected intermediate for the synthesis of modified nucleosides, which are crucial for the development of new pharmaceuticals. The protecting groups facilitate controlled reactions, ensuring the integrity of the nucleoside structure during the synthesis process.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5'-O-TRITYL-3'-O-MESYLTHYMIDINE is utilized as a key component in the creation of therapeutic agents. Its role in the synthesis of modified nucleosides contributes to the advancement of treatments for viral infections and cancer, given the potential of these modified nucleosides to target specific biological processes.
Used in Drug Development:
5'-O-TRITYL-3'-O-MESYLTHYMIDINE is employed as a building block in drug development, where its reactivity and structural features are harnessed to design and synthesize novel therapeutic agents. 5'-O-TRITYL-3'-O-MESYLTHYMIDINE's ability to be selectively deprotected allows for the precise modification of nucleoside structures, which is essential for optimizing drug efficacy and selectivity.
Used in the Pharmaceutical Industry:
Within the pharmaceutical industry, 5'-O-TRITYL-3'-O-MESYLTHYMIDINE is used as a precursor in the production of innovative drugs. Its involvement in the synthesis of modified nucleosides with therapeutic potential makes it a significant contributor to the development of new medications for various diseases, including viral infections and cancer.
Used in Research and Development:
In research and development settings, 5'-O-TRITYL-3'-O-MESYLTHYMIDINE serves as an important tool for exploring the chemical properties and reactivity of nucleosides. Its use in the synthesis of modified nucleosides aids scientists in understanding the structure-activity relationships of these compounds, thereby facilitating the discovery of new therapeutic agents.

InChI:InChI=1/C30H30N2O7S/c1-21-19-32(29(34)31-28(21)33)27-18-25(39-40(2,35)36)26(38-27)20-37-30(22-12-6-3-7-13-22,23-14-8-4-9-15-23)24-16-10-5-11-17-24/h3-17,19,25-27H,18,20H2,1-2H3,(H,31,33,34)

Upstream product

• 95585-76-5 2'-bromothymidine 
• 76-83-5 trityl chloride 
• 50-89-5 thymidine 
• 124-63-0 methanesulfonyl chloride 
• 7791-71-1 5'-O-tritylthymidine 

Downstream Products

• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 
• 132474-22-7 3'-O-ethyl-thymidine 5'-trityl ether 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 909256-85-5 O²,3'-anhydro-1-(5-O-trityl-2-deoxy-β-D-threo-pentofuranosyl)thymine 
• 7791-71-1 5'-O-tritylthymidine 
• 3056-17-5 stavudin 
• 25526-93-6 alovudine 
• 66503-47-7 1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 73971-78-5 6,3'-Imino-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 29706-84-1 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 34308-10-6 3'-O-mesylthymidine 
• 131933-46-5 3'-β-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine 

Relevant articles and documents

Intermediate preparation zidovudines and method

Disclosed is a method for preparing zidovudine (B). The method comprises the following steps: 1) 2'-halothymidine (A) is used as the raw material to obtain a compound of formula (I) by protecting the hydroxyl group thereof in the 5'-position; 2) the compound of formula (I) is subjected to the acylation of the hydroxyl group in the 3'-position to obtain a compound of formula (VI); 3) the compound of formula (VI) is dehalogenated to obtain a compound of formula (111); 4) the compound of formula (III) is subjected to an elimination reaction to obtain a compound of formula (IV); 5) the compound of formula (IV) is subjected to an azidation reaction to obtain a compound of formula (V); and 6) the compound of formula (V) is deprotected to obtain zidovudine (B); the specific reaction formula being shown in (C)below. In the formulae: X is a halogen, P1 is a protecting group for hydroxyl; and P2 is C1-C4 alkylsulfonyl, fluoro-C1-C4 alkylsulfonyl, arylsulfonyl or -CS-R, wherein R is C1-C4 alkyl.

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.

Synthesis and anti-HIV activity of triazolo-fused 3′,5′-cyclic nucleoside analogues derived from an intramolecular Huisgen 1,3-dipolar cycloaddition

Triazolo-fused 3′,5′-cyclic nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of nucleoside-derived azido-alkynes in a regio- and stereospecific manner. The thymine nucleoside base in these target compounds was transform

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.

Antiviral activity of various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-fluoro-2′,3′-didehydro-2′, 3′-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and human hepatitis B virus (HBV) replication

Despite the existence of successful vaccine and antiviral therapies, infection with hepatitis B virus (HBV) continues to be a major global cause of acute and chronic liver disease and high mortality. We synthesized and evaluated several lyxofuranosyl, 2′-fluoroxylofuranosyl, 3′- fluoroarabinofuranosyl, and 2′-fluoro-2′,3′-didehydro- 2′,3′-dideoxyribose pyrimidine nucleoside analogues for antiviral activities against hepatitis B virus. Among the compounds examined, 1-(2-deoxy-β-d-lyxofuranosyl)thymine (23), 1-(2-deoxy-β-d- lyxofuranosyl)-5-trifluoromethyluracil (25), 1-(2-deoxy-2-fluoro-β-d- xylofuranosyl)uracil (38), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)thymine (39), 2′,3′-dideoxy-2′,3′-didehydro-2′- fluorothymidine (48), and 2′,3′-dideoxy-2′,3′-didehydro- 2′-fluoro-5-ethyluridine (49) were found to possess significant anti-HBV activity against DHBV in primary duck hepatocytes with EC50 values of 4.1, 3.3, 40.6, 3.8, 0.2, and 39.0 μM, respectively. Compounds 23, 25, 39, 48, and 49 (EC50 = 41.3, 33.7, 19.2, 2.0-4.1, and 39.0 μM, respectively) exhibited significant activity against wild-type human HBV in 2.2.15 cells. Intriguingly, 25, 39, 48, and 49 retained sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and 48 emerged as an effective inhibitor of drug-resistant HBV with an EC50 of 4.1 μM. In contrast, 50% inhibition could not be achieved by lamivudine at 44 μM concentration in the drug-resistant strain. The compounds investigated did not show cytotoxicity to host cells up to the highest concentrations tested.

Method for sequencing DNA and RNA by synthesis

This invention relates to the field of nucleic acid chemistry, more specifically to the field of compositions and processes that are nucleic acid analogs. More specifically, this invention relates to compositions that allow the sequencing of oligonucleotides by synthesis, and processes for sequencing by synthesis that exploit these compositions. Most specifically, the instant invention discloses compositions of matter that are 5′-triphosphates of ribo- and 2′-deoxyribonucleosides wherein the 3′-OH group is replaced by a 3′-ONHR group in the alpha configuration, wherein R is either a H or CH3 group. Also disclosed are these triphosphates where the nucleobase carries, via a linker, a reporter groups, such as a fluorescent species that can be used in single- or multi-copy DNA sequencing, or a tag that can be visualized by ultramicroscopy. Also disclosed are processes that use these compositions to do sequencing by synthesis.

Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase

A number of 2′- and 3′-modified thymidine 5′-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2′-halogeno substituent and a 3′-azido function are the most favorable leads for further development of potent inhibitors of this enzyme.

Uracil- and thymine-substituted thymidine and uridine derivatives

The four possible 3'-uracil-1-yl and 3'-thymin-1-yl derivatives of 3'- deoxythymidine and the four analogous derivatives of 2'-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

Synthesis of pyrimidine 2'3'-dideoxy-2-thionucleosides

2'-Deoxyuridine 8a and thymidine 8b were converted in eight steps and in satisfactory overall yields into 2',3'-dideoxy-2-thiouridine (ddTU) 6a and 3'-deoxy-2-thiothymidine (ddTT) 6b, respectively. A three-step procedure is described for the conversion of ddTU 6a and ddTT 6b into the corresponding 2',3'-dideoxycytidine derivatives (ddTC 7a and ddMTC 7b, respectively) in good overall yield.

Synthesis of 3'-Fluoromethylthio-, 3'-Fluoromethylsulfinyl- and 3'-Fluoromethylsulfonyl-substituted 3'-Deoxythymidine

3'-Deoxy-3'-(fluoromethylthio)thymidine 2 is synthesized from 5'-O-benzoyl-3'-deoxy-3'-(methylsulfinyl)thymidine 9 by using DAST. 5'-O-Benzoyl-3'-deoxy-3'-(fluoromethylthio)thymidine is used as starting material for the synthesis of the sulfoxide 3 and the sulfone 4.Both sulfoxides 3A and 3B show a C3'-endo sugar conformation.