4449-43-8

Basic information

• Product Name: ALPHA-THYMIDINE
• Synonyms: 1-[2-DEOXY-ALPHA-D-RIBOFURANOSYL]-5-METHYLURACIL;ALPHA-THYMIDINE;A-thymidine;alpha-thymidinecrystalline;1-(2-Deoxy-α-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;1-(2-Deoxy-α-D-erythro-pentofuranosyl)thymine
• CAS NO: 4449-43-8
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.23
• Mol File: 4449-43-8.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.452g/cm³
• Refractive Index: 1.584
• CAS DataBase Reference: ALPHA-THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-THYMIDINE(4449-43-8)
• EPA Substance Registry System: ALPHA-THYMIDINE(4449-43-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4449-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biotechnology Industry:
ALPHA-THYMIDINE is used as a key component in the synthesis of oligonucleotides containing α-Thymidine. Its incorporation into these molecules allows for the development of novel therapeutic agents and diagnostic tools, contributing to advancements in drug discovery and the study of genetic diseases.
Used in Research and Development:
ALPHA-THYMIDINE serves as an essential research tool for scientists working on the study of nucleic acids, DNA replication, and other related fields. Its unique properties enable researchers to investigate the mechanisms of various biological processes and develop a deeper understanding of the molecular basis of life.
Used in Synthesis of Nucleic Acid Analogs:
ALPHA-THYMIDINE is used as a building block in the synthesis of nucleic acid analogs, which are crucial for the development of new drugs and therapies targeting various diseases, including cancer and viral infections. These analogs can be designed to have specific properties, such as improved stability or targeted delivery, to enhance their therapeutic potential.

InChI:InChI=1/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8-/m0/s1

Upstream product

• 4784-41-2 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine 
• 65-71-4 thymin 
• 433733-94-9 3',5'-di-O-acetyl-β-L-thymidine 
• 50571-26-1 5'-DMT-thymidine-3'-H-phosphonate 
• 50-89-5 thymidine 
• 68027-40-7 2,4-di-O-trimethylsilylthymine 
• 1062488-85-0 C₂₆H₂₆N₂O₇ 
• 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 
• 7791-71-1 5'-O-tritylthymidine 
• 271248-27-2 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-2'-O-(phenoxythiocarbonyl)-L-uridine 
• 271248-26-1 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-L-uridine 

Downstream Products

• 52474-36-9 1-[2-deoxy-5-O-(4-methoxytrityl)-α-D-erythro-pentofuranosyl]thymine 
• 134031-87-1 3'-O-(4,4'-dimethoxytrityl)-α-thymidine 
• 201219-77-4 5'-O-acetyl-3'-O-(4,4'-dimethoxytrityl)-α-thymidine 
• 201219-79-6 Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 201219-83-2 1-{(2S,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-4-[(pyren-2-ylmethyl)-amino]-1H-pyrimidin-2-one 
• 201219-81-0 Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 
• 114988-00-0 Phosphoramidous acid (2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester 
• 906354-75-4 5-O-tert-butyldiphenylsilyl-α-thymidine 
• 1416441-60-5 C₁₆H₁₈N₄O₈S 
• 1416442-52-8 C₂₄H₂₅ClN₄O₆ 
• 1416442-54-0 C₂₄H₂₅ClN₄O₆ 
• 1416442-56-2 C₂₅H₂₈N₄O₇ 
• 1416442-58-4 C₂₈H₃₄N₄O₆ 
• 1416441-63-8 C₁₇H₁₈N₄O₇ 

Relevant articles and documents

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

Interaction of α-Thymidine Inhibitors with Thymidylate Kinase from Plasmodium falciparum

Plasmodium falciparum thymidylate kinase (PfTMK) is a critical enzyme in the de novo biosynthesis pathway of pyrimidine nucleotides. N-(5′-Deoxy-α-thymidin-5′-yl)-N′-[4-(2-chlorobenzyloxy)phenyl]urea was developed as an inhibitor of PfTMK and has been reported as an effective inhibitor of P. falciparum growth with an EC50 of 28 nM [Cui, H., et al. (2012) J. Med. Chem. 55, 10948-10957]. Using this compound as a scaffold, a number of derivatives were developed and, along with the original compound, were characterized in terms of their enzyme inhibition (Ki) and binding affinity (KD). Furthermore, the binding site of the synthesized compounds was investigated by a combination of mutagenesis and docking simulations. Although the reported compound is indicated to be highly effective in its inhibition of parasite growth, we observed significantly lower binding affinity and weaker inhibition of PfTMK than expected from the reported EC50. This suggests that significant structural optimization will be required for the use of this scaffold as an effective PfTMK inhibitor and that the inhibition of parasite growth is due to an off-target effect.

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.

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.

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.

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.

Participation of an additional 4′-hydroxymethyl group in the cleavage and isomerization of ribonucleoside 3′-phosphodiesters

4′-(Hydroxymethyl)uridylyl-3′,5′-thymidine, an RNA model bearing an extra hydroxymethyl group at the 4′-position of the 3′-linked nucleoside, has been prepared and its cleavage and isomerization reactions studied over a wide pH range (from 0 to 12). Overa

DERIVATIVES OF PHENYL (THIO) UREA DEOXYTHYMIDINE AND USE THEREOF AS ANTIMALARIALS

Deoxythymidine derivatives according to formula (I) are disclosed. wherein: X may be O or S; and R1, R2, R3, R4 and R5 may each be independently selected from H, halo, C1-C6 alkyl, C1-C6 haloalkyl, nitro, phenyl, heteroaryl, substituted heteroaryl wherein the substituents may be C1-C6 alkyl or C1-C6 haloalkyl, benzyl, -CH2OAr, -OR6 and six-membered ring heterocyclic groups containing 1 or more O and/or N heteroatoms wherein any N heteroatom may be C1-C6 alkyl-substituted; and R6 may be selected from C1-C6 alkyl, phenyl, six-membered ring heterocyclic groups containing at least one O heteroatom, benzyl and substituted benzyl wherein the substituents may be halo, C1-C6 alkyl or C1-C6 alkoxy; R7 may be H or C1-C6 alkyl; and the stereochemistry of the bond depicted as ? is either α or β. Such derivatives have shown good inhibitory activity against malaria-causing parasites, e.g. Plasmodium falciparum, but have shown low levels of toxicity to human cells.

Synthesis and evaluation of α-thymidine analogues as novel antimalarials

Plasmodium falciparum thymidylate kinase (PfTMPK) is a key enzyme in pyrimidine nucleotide biosynthesis. 3-Trifluoromethyl-4-chloro-phenyl-urea- α-thymidine has been reported as an inhibitor of Mycobacterium tuberculosis TMPK (MtTMPK). Starting from this

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.