97974-93-1

Usage

Uses

Used in Pharmaceutical Industry:
3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE is used as a reactant/reagent for the preparation of hydroxyl-group-functionalized nucleoside analogs. This is achieved through an efficient orthogonal protecting strategy, which allows for the selective deprotection and functionalization of the hydroxyl groups in the molecule. The resulting nucleoside analogs can exhibit improved biological activity and selectivity, making them potential candidates for the development of new antiviral, anticancer, and other therapeutic agents.
Used in Chemical Research:
3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE is also used as a research tool in the field of organic chemistry and nucleic acid chemistry. Its unique structure and reactivity make it an interesting target for the development of new synthetic methods, as well as for the study of the interactions between nucleoside analogs and biological macromolecules, such as DNA and RNA. This can lead to a better understanding of the molecular mechanisms underlying the biological activity of these compounds and the discovery of new therapeutic targets.
Used in DNA Technology:
3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE can be incorporated into oligodeoxynucleotides, which are short, synthetic DNA fragments used in various molecular biology techniques. The presence of the hydroxyl-group-functionalized nucleoside analogs can enhance the stability of the DNA duplex, which is important for applications such as PCR, DNA sequencing, and the development of DNA-based sensors and devices. This can lead to improved performance and new applications in the field of DNA technology.

Upstream product

• 3056-12-0 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 
• 23956-12-9 5-(2-hydroxyethyl)-uracil 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 259737-41-2 5-(2-Acetoxyethyl)-2,4-dimethoxypyrimidine 
• 259737-43-4 5-(2-Acetoxyethyl)-4-methoxypyrimidin-2(1H)-one 
• 259737-44-5 5-(2-Hydroxyethyl)-4-methoxypyrimidin-2(1H)-one 
• 108008-56-6 2,4-dimethoxy-5-(2-hydroxyethyl)pyrimidine 
• 259737-45-6 1-(3,5-Di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-4-methoxypyrimidin-2-one 

Downstream Products

• 914381-97-8 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidine-2,4-dione 
• 53438-96-3 5-(2-bromoethyl)uracil 

Relevant academic research and scientific papers

Hydroxyl-functionalized DNA: An efficient orthogonal protecting strategy and duplex stability

Tert-butyldiphenylsilyl (TBDPS) was found to be an effective orthogonal protecting strategy for the 5-substituted hydroxyl groups of de novo synthesized deoxyuridine analogues 1-3 and 7-(3-hydroxypropynyl)- of 8-aza-7- deazadeoxyadenosine 4 for their inco

Synthesis of 4-O-methyl-protected 5-(2-hydroxyethyl)-2'-deoxyuridine derivatives and their nucleophilic fluorination to 5-(2-fluoroethyl)-2'- deoxyuridine

The novel pyrimidine base, 5-(2-hydroxyethyl)-4-methoxypyrimidin-2(1H)- one (7) was prepared from the pyrimidine derivative 2 via a three step synthesis in 72% yield. Glycosylation of 7 with an α-chlorosugar provided the 4-O-methyl-protected pyrimidine nucleoside 8 in 78% yield with a β:α ratio ranging from 1.5:1 to 2:1. A complete cleavage of the 4-methoxy group of alcohol 8 was achieved using NaI and trimethylsilyl chloride. The synthesis of 14, an analog of 8, was also possible by using N,O- bis(trimethylsilyl)trifluoroacetimide as silylating reagent and 3,5-di-O-p- chlorobenzoyl-2-deoxy-α-D-erythro-pentofuranosyl chloride as the sugar moiety. A slightly improved ratio of β/α (>2:1) and a yield of 54% of 14 was obtained. The two key precursors for nucleophilic fluorination, the tosylate 9 and triflate 10, were obtained in 87 and 17% yield, respectively. NOE results of 10β and 10α indicated that H-1' of the deoxyribosyl residue interacted strongly with one of the two protons on C-8 of the 5-ethyl side chain. This interaction was even stronger than that between H-1' and H-2'. The unusual downfield chemical shift of C-1' in 13C NMR can not be explained by the structure shown in Scheme 3. Nucleophilic fluorination of the tosylate 9α under phase transfer catalyzed conditions provided the fluorinated product 11α (5%), the base-induced elimination product 12α (24%), and unexpectedly the chloro-substituted product 13α (26%).

5-(Haloalkyl)-2'-deoxyuridines: A Novel Type of Potent Antiviral Nucleoside Analogue

Syntheses of 5-(2-haloethyl)-2'-deoxyuridines, 5-(3-chloropropyl)-2'-deoxyuridines, and 5-(2-chloroethyl)-2'-deoxycytidine are described.The antiviral activities of these compounds were determined in cell culture against herpes simplex virus types 1 and 2