2560-60-3

Usage

Uses

Used in Biochemical Research:
Uridine, 5-fluoro-, 2',3',5'-tribenzoate is used as a research tool for studying nucleotide metabolism and signaling pathways. Its unique structure allows for the investigation of the effects of modifications on uridine's biological activity and interactions with enzymes and other biomolecules.
Used in Pharmaceutical Research:
Uridine, 5-fluoro-, 2',3',5'-tribenzoate is used as a potential drug candidate in the development of new therapeutic agents. Its modified structure may offer advantages in terms of stability, bioavailability, or target specificity compared to the parent compound, uridine.
Used in Drug Development:
Uridine, 5-fluoro-, 2',3',5'-tribenzoate is used as a starting material or intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its chemical properties can be further modified to create new compounds with improved pharmacological properties.
It is important to handle and use Uridine, 5-fluoro-, 2',3',5'-tribenzoate with caution, following proper safety protocols and guidelines to ensure the safety of researchers and the environment.

Upstream product

• 114762-36-6 2,3,5-tri-O-benzoyl-D-ribofuranosyl fluoride 
• 17242-85-2 5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 316-46-1 5-fluorouridine 
• 132842-55-8 4-ethoxy-5-fluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyrimidinone 
• 137653-67-9 2',3',5'-tri-O-benzoyl-3-benzyl-5-fluorouridine 
• 137653-66-8 2',3',5'-tri-O-benzoyl-3-ethyl-5-fluorouridine 
• 137653-65-7 2',3',5'-tri-O-benzoyl-N⁽³⁾-methyl-5-fluorouridine 
• 137653-81-7 (1S,6S)-4-benzyl-6-fluoro-7,7,8,8-tetramethyl-2-(β-D-ribofuranosyl)-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 137653-81-7 (1R,6R)-4-benzyl-6-fluoro-7,7,8,8-tetramethyl-2-(β-D-ribofuranosyl)-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 137653-74-8 4-benzyl-6-fluoro-7,7,8,8-tetramethyl-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 137653-73-7 4-ethyl-6-fluoro-7,7,8,8-tetramethyl-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 137653-72-6 6-fluoro-4,7,7,8,8-pentamethyl-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 2341-22-2 5-fluorocytidine 
• 53294-73-8 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluorocytosine 

Relevant academic research and scientific papers

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.

A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation

A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.

Synthesis and structure-activity relationship of uracil nucleotide derivatives towards the identification of human P2Y6 receptor antagonists

P2Y6 receptor (P2Y6-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y6-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5′-α,β-methylene-diphosphonate, 16 and 23, or lack of 2′-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y6-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y6-R (IC50 112 μM) versus P2Y2/4-Rs. In summary, we have established a comprehensive SAR for hP2Y6-R ligands towards the development of hP2Y6-R antagonists.

NEW PRODUCTION METHOD FOR PYRIMIDINE NUCLEOSIDE DERIVATIVES

PROBLEM TO BE SOLVED: To provide a method for producing pyrimidine nucleoside derivatives with excellent handleability. SOLUTION: A glycosyl donor of which OH groups at positions 1 and 2 are acylated and other OH groups are protected and a silylated pyrimidine derivative are reacted in the presence of an acid azole/pyridine conjugate of the following general formula (1) or (2) and a solvent. Acid azole/pyridine conjugate is excellent in handleability because it has no or low hygroscopicity. In the formula (1), A is -O- or -S-, in the formulae (1) and (2), R1-R8 are hydrocarbon groups which may be substituted, R1-R8 may form a ring by binding to other R1-R8, the acid azole/pyridine conjugate may comprise plurality of formula (1) and/or formula (2) as partial structures. Further, it may be bonded to a carrier via R1-R8. COPYRIGHT: (C)2015,JPO&INPIT

Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate

Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5- phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales.

One-flow, multistep synthesis of nucleosides by Bronsted acid-catalyzed glycosylation

Nucleosides in flow: A general, scalable method of Bronsted acid-catalyzed nucleoside formation is described. Because of the high reaction temperatures readily available to the flow reaction format, mild Bronsted acids, particularly pyridinium triflates, can be used. A one-flow multistep synthesis of unprotected nucleosides is also reported (see scheme).

Condensation of 1-Fluorofuranones and Silylated Nucleobases Catalyzed by Tetrafluorosilane

The title reaction provides a generally useful tool for nucleoside synthesis.The stereoselectivities are highly influenced by the fluoride substrates, and steric course of the reaction of O-benzylated ribofuranosyl fluoride is solvent dependent.