1748-04-5

Basic information

• Product Name: 2',3',5'-TRI-O-BENZOYLURIDINE
• Synonyms: uridine 2',3',5'-tribenzoate;2'',3'',5''-TRI-O-BENZOYLURIDINE 96%;2',3',5'-Tribenzoyluridine, 96%;[4-(benzoyloxy)-2-(benzoyloxymethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate;[4-(benzoyloxy)-2-(benzoyloxymethyl)-5-(2,4-dioxopyrimidin-1-yl)tetrahydrofuran-3-yl] benzoate;2-[(benzoyloxy)methyl]-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate;benzoic acid [4-(benzoyloxy)-2-(benzoyloxymethyl)-5-(2,4-diketopyrimidin-1-yl)tetrahydro;benzoic acid [5-(2,4-dioxo-1-pyrimidinyl)-4-(oxo-phenylmethoxy)-2-[(oxo-phenylmethoxy)methyl]-3-tetrahydrofuranyl] ester
• CAS NO: 1748-04-5
• Molecular Formula: C₃₀H₂₄N₂O₉
• Molecular Weight: 556.52
• EINECS: 217-131-6
• Mol File: 1748-04-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.44g/cm³
• Storage Temp.: −20°C
• Solubility: DMSO, Methanol
• CAS DataBase Reference: 2',3',5'-TRI-O-BENZOYLURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-TRI-O-BENZOYLURIDINE(1748-04-5)
• EPA Substance Registry System: 2',3',5'-TRI-O-BENZOYLURIDINE(1748-04-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1748-04-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2',3',5'-Tri-O-benzoyluridine is used as an intermediate in the synthesis of uridine (U829910) for its role in the development of pharmaceuticals targeting various diseases and conditions. Uridine plays a crucial role in the synthesis of RNA and is involved in numerous cellular processes, making it a valuable compound for drug development.
Used in Research and Development:
In the field of research and development, 2',3',5'-Tri-O-benzoyluridine is utilized as a key compound in the study of RNA structure, function, and its interactions with other biomolecules. Its role in the synthesis of uridine allows researchers to explore the potential applications of uridine and its derivatives in understanding and treating various diseases.
Used in Biochemical Applications:
2',3',5'-Tri-O-benzoyluridine is also used in various biochemical applications, such as the development of nucleotide analogs and the study of enzyme mechanisms involving RNA and its components. Its structural similarity to uridine makes it a valuable tool for investigating the roles of nucleosides in biological systems.

Upstream product

• 98-88-4 benzoyl chloride 
• 58-96-8 uridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 66-22-8 uracil 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 21052-18-6 2-thio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-(3H)pyrimidine-2,4-dione 
• 613-90-1 benzoyl cyanide 
• 532-32-1 sodium benzoate 
• 259856-99-0 1-(β-L-arabinofuranosyl-2-O-methanesulfonyl-3,5-di-O-benzoyl)uracil 
• 35939-60-7 2-amino-β-L-arabinofurano[1',2':4,5]oxazoline 
• 31501-46-9 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 31615-96-0 3',5'-di-O-benzoyl-2,2'-anhydro-L-uridine 
• 870135-04-9 4-N-pivalyl-2',3',5'-tri-O-benzoylcytidine 
• 774235-34-6 1-[(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)methyl]acetate 

Downstream Products

• 15049-50-0 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil 
• 99679-98-8 4-(imidazol-1-yl)-2-pyrimidinone riboside 
• 135073-77-7 5-(2,6-Dichlorobenzoyl)-2',3',5'-tri-O-benzoyluridine oxime 
• 137653-64-6 2',3',5'-tri-O-benzoyl-3-benzyluridine 
• 137653-63-5 2',3',5'-tri-O-benzoyl-3-ethyluridine 
• 137653-62-4 2',3',5'-tri-O-benzoyl-3-methyluridine 
• 38953-75-2 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 5552-05-6 2’,5’-dibenzoyluridine 
• 54618-06-3 5′-O-benzoyluridine 
• 54618-11-0 3’,5’-dibenzoyluridine 
• 58-96-8 uridine 
• 50408-20-3 2',3'-di-O-benzoyluridine 
• 28616-91-3 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil 
• 15049-50-0 O^2'_,O3'_,O5'-tribenzoyl-4-thio-uridine 

Relevant articles and documents

Inhibition of tyrosyl-DNA phosphodiesterase 1 by lipophilic pyrimidine nucleosides

Inhibition of DNA repair enzymes tyrosyl-DNA phosphodiesterase 1 and poly(ADP-ribose) polymerases 1 and 2 in the presence of pyrimidine nucleoside derivatives was studied here. New effective Tdp1 inhibitors were found in a series of nucleoside derivatives possessing 2′,3′,5′-tri-O-benzoyl-d-ribofuranose and 5-substituted uracil moieties and have half-maximal inhibitory concentrations (IC50) in the lower micromolar and submicromolar range. 2′,3′,5′-Tri-Obenzoyl- 5-iodouridinemanifested the strongest inhibitory effect on Tdp1 (IC50 = 0.6 μM). Adecrease in the number of benzoic acid residues led to a marked decline in the inhibitory activity, and pyrimidine nucleosides lacking lipophilic groups (uridine, 5-fluorouridine, 5-chlorouridine, 5-bromouridine, 5-iodouridine, and ribothymidine) did not cause noticeable inhibition of Tdp1 (IC50 > 50 μM). No PARP1/2 inhibitors were found among the studied compounds (residual activity in the presence of 1mMsubstances was 50-100%). Several O-benzoylated uridine and cytidine derivatives strengthened the action of topotecan on HeLa cervical cancer cells.

An efficient method for the synthesis of β-D-ribonucleosides catalyzed by metal iodides

Several β-D-ribonucleosides were synthesized in high yields under mild conditions by N-glycosylations of methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI2, SbI3 or TeI4. A deprotection of N6-benzoyl group of coupling product took place to a considerable extent when N6-benzoyl-N6,N9-bis(trimethylsilyl)adenine was employed as a nucleoside base using SnI2 or SnCI2 as a catalyst while it was minimized when SbI3 or TeI4 was used. Further, the N-glycosylation of 1 with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile.

Tin(II) Chloride Catalyzed Synthesis of β-D-Ribonucleosides

Several β-D-ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate and trimethylsilylated nucleoside bases such as pertrimethylsilylated uracil and adenine under mild conditions by using a catalytic amount of tin(II) chloride, a weak Lewis acid.

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides

Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed.

Ortho-(1-phenylvinyl)benzoate glycosylation donor, and preparation method and application thereof

The invention discloses an ortho-(1-phenylvinyl)benzoate glycosylation donor, and a preparation method and an application thereof in a glycosylation reaction. The ortho-(1-phenylvinyl)benzoate glycosylation donor is stable, is easy to prepare and store, and is widely applied to the construction of various oxygen glucosides and nucleoside (nitrogen glucoside) glycosidic bonds. The leaving group ofthe donor is an alkenyl ester, has a high activity, and can be combined with thioglycoside or n-pentenyl ether glucoside through a one-pot glycosylation reaction to synthesize oligosaccharide. The glycosylation reaction conditions are mild, and receptors sensitive to acid and electrophilic reagents can tolerate the glycosylation reaction conditions.

3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use

The invention discloses a 3-methyluridine and 4-methylcytidine nucleosides compound and a synthesis method and pharmaceutical application thereof, belonging to the field of medicinal chemistry. The compound has a structural formula as shown in the specification. The compound has the effects of simultaneously modifying sugar rings and basic groups, increasing the activity of the compound and reducing the toxicity, provides a good application prospect for development of like medicines and can be applied to preparation of anti-HBV (Hepatitis B virus) medicines. The synthesis method is simple and feasible and provides conditions for mass synthesis of the compound.

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.

Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides

Pyrimidine nucleosides are synthesized by using propargyl 1,2-orthoesters and Au(III) salt as a catalyst. Strategically positioned 1,2-orthoesters are found to yield only 1,2-trans nucleosides and enable preparation of 2′-OH containing pyrimidine nucleosides. The glycosyl donor employed in this study is stable and easily accessible. The identified high-yielding protocol is mild, diastereoselective, and catalytic.

A Reverse Strategy for synthesis of nucleosides based on n-pentenyl orthoester donors

Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as -78°C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized.