76756-28-0

Basic information

• Product Name: 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4(1H,3H)-pyrimidinedione, 1-(2-deoxypentofuranosyl)-5-phenyl-
• CAS NO: 76756-28-0
• Molecular Formula: C₁₅H₁₆N₂O₅
• Molecular Weight: 304.2979
• Mol File: 76756-28-0.mol
• Article Data: 19

Chemical Properties

• Density: 1.442g/cm³
• Refractive Index: 1.635
• CAS DataBase Reference: 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione(76756-28-0)
• EPA Substance Registry System: 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione(76756-28-0)

Safety Data

• Hazardous Substances Data: 76756-28-0(Hazardous Substances Data)

Usage

General Description

1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione, also known as dThd or deoxythymidine, is a nucleoside compound that is a crucial building block in the synthesis of DNA. It is composed of a deoxyribose sugar molecule attached to a thymine base, and it is essential for the replication and transmission of genetic information. Deoxythymidine is commonly found in the genetic material of all living organisms and plays a vital role in cell division and growth. It is also used in laboratory experiments and medical treatments as a pharmaceutical agent for various genetic and viral diseases. Furthermore, it has been extensively studied for its potential applications in cancer therapy and antiviral treatments.

Upstream product

• 591-50-4 iodobenzene 
• 65505-76-2 C⁵-chloromercuri-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 934-56-5 trimethyl(phenyl)stannane 
• 78824-31-4 di-O-trimethylsilyl-5-iodo-2'-deoxyuridine 
• 98-80-6 phenylboronic acid 
• 137100-79-9 3'-O,5'-O,N³-tritoluoyl-5-iodo-2'-deoxyuridine 
• 76772-94-6 5-Iodo-4-trimethylsilanyloxy-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 
• 71-43-2 benzene 
• 951-78-0 2'-deoxyuridine 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 62-53-3 aniline 

Downstream Products

• 76756-31-5 C₁₅H₁₅N₂O₈P^(2-) 
• 1574218-93-1 5′-(4,4′-dimethoxytrityloxymethyl)-5-phenyl-2′-deoxyuridine 
• 1574218-98-6 3′-O-(P-(2-cyanoethoxy)-N,N′-diisopropylaminophosphinyl)-5′-(4,4′-dimethoxytrityl)-5-phenyl-2′-deoxyuridine 

Relevant articles and documents

Supported synthesis and functionnalization of 2″-deoxyuridine by Suzuki-Miyaura cross-coupling

The synthesis and modification of 2′-deoxyuridine has been realized under Suzuki-Miyaura palladium-catalyzed cross-coupling conditions. Using Pd(PPh3)4 and Na2CO3, 5-iodo-2′-deoxyuridine bound to solid support is coupled with various boronic acids to give

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR THE TREATMENT OF DISEASE

This invention relates to compounds and compositions for the induction of expression of a pattern recognition receptor (e.g., STING) and methods of use thereof.

High-affinity RNA targeting by oligonucleotides displaying aromatic stacking and amino groups in the major groove. Comparison of triazoles and phenyl substituents

Three 5-modified 2′-deoxyuridine nucleosides were synthesized and incorporated into oligonucleotides and compared with the previously published 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomer W. The introduction of an aminomethyl group on the phenyl group led to monomer X, which was found to thermally stabilize a 9-mer DNA:RNA duplex, presumably through the partial neutralization of the negative charge of the backbone. By also taking advantage of the stacking interactions in the major groove of two or more of the monomer X, an extremely high thermal stability was obtained. A regioisomer of the phenyltriazole substituent, that is the 5-(4-phenyl-1,2,3-triazol-1-yl)- 2′-deoxyuridine monomer Y, was found to destabilize the DNA:RNA duplex significantly, but stacking in the major groove compensated for this when two to four monomers were incorporated consecutively. Finally, the 5-phenyl-2′-deoxyuridine monomer Z was incorporated for comparison, and it was found to give a more neutral influence on duplex stability indicating less efficient stacking interactions. The duplexes were investigated by CD spectroscopy and MD simulations.