3424-98-4

Usage

Uses

Used in Antiviral Applications:
2'-Deoxy-L-thymidine is used as a nucleoside analog for the inhibition of HBV replication. It is particularly effective as an antiviral agent against hepatitis B virus, helping to control the viral load and prevent the progression of the disease.
Used in Hepatitis B Treatment:
In the pharmaceutical industry, 2'-Deoxy-L-thymidine is used as an active ingredient in the drug Telbivudine (brand name Novirio), which is prescribed for the once-daily oral treatment of chronic hepatitis B virus (HBV) infection. It has been shown to be more effective than lamivudine or adefovir and less likely to cause resistance, making it a preferred choice for treating HBV infections.
Used in Research and Development:
2'-Deoxy-L-thymidine is also utilized in the research and development of new antiviral drugs and therapies. Its unique properties as a nucleoside analog and inhibitor of HBV replication make it a valuable compound for studying the mechanisms of viral replication and the development of novel treatments for viral infections.

Originator

Idenix (US)

Upstream product

• 271248-28-3 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-L-thymidine 
• 65-71-4 thymin 
• 271248-26-1 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-L-uridine 
• 271248-27-2 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-2'-O-(phenoxythiocarbonyl)-L-uridine 
• 7791-71-1 5'-O-tritylthymidine 
• 1062488-85-0 C₂₆H₂₆N₂O₇ 
• 433733-94-9 3',5'-di-O-acetyl-β-L-thymidine 
• 68027-40-7 2,4-di-O-trimethylsilylthymine 
• 50571-26-1 5'-DMT-thymidine-3'-H-phosphonate 
• 50-89-5 thymidine 
• 143156-51-8 C₁₂H₁₈N₂O₆ 
• 817622-48-3 C₂₀H₃₀N₂O₇ 
• 40093-95-6 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine 
• 3056-13-1 1-(2-deoxy-3,5-di-p-toluoyl-β-L-ribose)-5-methyluracil 

Downstream Products

• 131607-27-7 1-((2S,4R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 52417-09-1 3'-O-(4,4'-dimethoxytriphenylmethyl)-5'-O-fluorenylmethoxycarbonylthymidine 
• 1333995-40-6 C₂₁H₂₄ClN₈O₆P 
• 1333995-50-8 C₂₁H₂₆N₉O₆P 
• 1333995-78-0 C₂₁H₂₅ClN₉O₆P 
• 1333995-93-9 C₂₁H₂₇N₁₀O₆P 
• 1333996-11-4 C₂₁H₂₇N₆O₈P 
• 132979-39-6 1-(3-azido-2,3-dideoxy-β-L-erythro-pentofuranosyl)thymine 
• 1356470-37-5 3',5'-di-O-acetyl-5-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)methyl)-2'-deoxy-β-L-uridine 
• 1356470-38-6 5-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)methyl)-2'-deoxy-β-L-uridine 
• 1187-84-4 S-methyl-L-cysteine 
• 958-74-7 3-methylthymidine 
• 116454-12-7 5'-(2,6-dichlorobenzoyl)-deoxythymidine 

Relevant academic research and scientific papers

Meteorite-catalyzed intermoleculartrans-glycosylation produces nucleosides under proton beam irradiation

Di-glycosylated adenines act as glycosyl donors in the intermoleculartrans-glycosylation of pyrimidine nucleobases under proton beam irradiation conditions. Formamide and chondrite meteorite NWA 1465 increased the yield and the selectivity of the reaction

Synthesis method of beta-thymidine

The invention discloses a synthesis method of beta-thymidine. The synthesis method takes trimethylchlorosilane and 5-methyluracil as raw materials to react; in a reaction line process, tetraacetylribose, trifluoromethanesulfonic acid, N,N-dimethylformamide and acetylchloride are introduced; then hydrogenation reaction and hydrolysis reaction are carried out to finally obtain a beta-thymidine finished product and the yield is 89 percent. Compared with an existing synthesis method, the synthesis method of the beta-thymidine has the advantages that the price of raw materials is low, the content of the beta-thymidine in the final product is high, and pollution to the environment in a production process is small; in a synthesis process, the content of generated impurities is less. According to the synthesis method disclosed by the invention, an obtained result is stable and the operation is simple; demands on equipment and preparation environments are not strict so that large-scale popularization is facilitated.

METHODS FOR THE TREATMENT OF HEPATITIS B AND HEPATITIS D VIRUS INFECTIONS

It is disclosed a method for treating hepatitis B virus infection or hepatitis B virus/hepatits delta virus co-infection, the method comprising administering to a subject in need of such treatment a first pharmaceutically acceptable agent that comprises at least one phosphorothioated nucleic acid polymer and a second pharmaceutically acceptable agent that comprises at least one nucleoside/nucleotide analog HBV polymerase inhibitor.

Method for preparing telbivudine

The invention relates to a method for preparing telbivudine. The reaction mechanism is as shown in the specification specifically. Compared with a method of the prior art, the method provided by the invention has the advantages that firstly, all raw materials are low in cost and can be easily obtained from the market; secondly, reaction of different steps is normal reaction, and the reaction steps are simple and easy to implement; and thirdly, production requirements can be met by using normal preparation equipment, the production is easy to control, and industrial production can be achieved.

Method for preparing high-purity telbivudine compound

The invention belongs to the technical field of medicine and provides a method for preparing a high-purity telbivudine compound. The method includes the steps that an LTD-4 compound serves as the raw material and reacts with thymine subjected to silicification protection, and an intermediate, namely an LTD-5 compound, can be obtained; then, through deprotection reaction, the telbivudine compound is obtained after post-processing, wherein MeONa serves as an alkaline reagent of the deprotection reaction, and strong-acidity resin serves as a dealkalization reagent. The method simplifies the production process, the yield of each step is high, and a target product high in purity and yield is obtained. Please see the structural formula in the description.

PROCESS FOR PREPARING L-NUCLEIC ACID DERIVATIVES AND INTERMEDIATES THEREOF

A novel method has been found to produce 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now, is possible.

Synthesis of L-2′-deoxypentofuranonucleoside derivatives of thymine from D-glucose

Convergent synthesis of L-2′-deoxypentofuranonucleoside derivatives of thymine was carried out from D-glucose via 6-O-toluoyl-3-deoxy-1,2-O- isopropylidene-β-L-lyxo-hexofuranose as a key intermediate. Copyright Taylor & Francis Group, LLC.

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

2'-deoxy-L-nucleosides

This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH2, NHR′, or NR′R″Z is H, F, Cl, Br, I, CN, or NH2. R is hydrogen, halogen, lower alkyl of C1-C6 or aralkyl, NO2, NH2, NHR′, NR′R″, OH, OR, SH, SR, CN, CONH2, CSNH2, CO2H, CO2R′, CH2CO2H, CH2CO2R′, CH═CHR, CH2CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C1-C6. R13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

Regioselective enzymatic acylation of β-L-2′-deoxynucleosides: Application in resolution of β-D/L-2′-deoxynucleosides

(Chemical Equation Presented) A practical synthesis of β-L-3′- and β-L-5′-O-levulinyl-2′-deoxynucleosides has been described for the first time through enzymatic acylation and/or hydrolysis processes. It is noteworthy that the different behavior exhibited by Pseudomonas cepacia lipase in the acylation of D- and L-nucleosides allows the parallel kinetic resolution of D/L-nucleosides.