5552-05-6

Basic information

• Product Name: Uridine, 2',5'-dibenzoate
• CAS NO: 5552-05-6
• Molecular Formula: C23H20N2O8
• Molecular Weight: 452.42
• Mol File: 5552-05-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Uridine, 2',5'-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 2',5'-dibenzoate(5552-05-6)
• EPA Substance Registry System: Uridine, 2',5'-dibenzoate(5552-05-6)

Safety Data

• Hazardous Substances Data: 5552-05-6(Hazardous Substances Data)

Usage

General Description

Uridine, 2',5'-dibenzoate is a chemical compound that is derived from uridine, a nucleoside found in RNA. Uridine, 2',5'-dibenzoate is commonly used in the field of biochemistry and molecular biology as a precursor for the synthesis of various nucleoside derivatives. It is also used as a building block for the production of nucleic acid analogues and other pharmaceuticals. Uridine, 2',5'-dibenzoate is known for its potential therapeutic applications, particularly for its neuroprotective and anti-inflammatory properties. Additionally, it has been studied for its potential effects on mood and cognition. Overall, this chemical compound plays a crucial role in the development of new pharmaceuticals and in the study of RNA-related processes.

Upstream product

• 1748-04-5 tribenzoyl uridine 
• 98-88-4 benzoyl chloride 
• 58-96-8 uridine 

Downstream Products

• 100778-59-4 C₂₄H₂₂ClN₂O₁₀P 
• 115288-15-8 C₄₈H₄₃N₄O₁₈P 

Relevant articles and documents

Kilogram-Scale Synthesis of 2′- C-Methyl- arabino-Uridine from Uridine via Dynamic Selective Dipivaloylation

We report a practical 3′,5′-diprotection strategy suitable for the kilogram-scale preparation of 2′-C-methyl-arabino-uridine, a key intermediate in the synthesis of the HCV NS5B inhibitor uprifosbuvir. Starting from uridine, dipivaloylation afforded an ～2:1 mixture of 3′,5′- and 2′,5′-dipivaloyluridine. Subjecting this mixture to TEMPO/bleach oxidation promoted a dynamic acylation migration-selective oxidation to afford the 2′-ketone in 65% yield. Alternatively, treatment with 1 equiv of BF3 etherate led to the crystallization-driven equilibration and precipitation of 3′,5′-dipivaloyluridine·BF3 complex in a >50:1 ratio. After salt break, this mixture was oxidized in the presence of TEMPO/AcOOH to afford the 2′-ketone in 90% yield. Subsequent α-facial-selective methylation with MeMgBr/MnCl2 afforded 3′,5′-dipivaloylated 2′-C-methyl-arabino-uridine 12. This three-step process was successfully demonstrated on a multikilogram scale to afford the key intermediate for the manufacture of uprifosbuvir.

Regioselective Mitsunobu Reaction of Partially Protected Uridine

Mitsunobu reaction of partially acylated uridine proceeds with high regioselectivity for intramolecular SN2 anhydro linkage closuring. Under the reaction conditions, an isomeric mixture of diacyl uridine derivatives with either free 2′- or 3′-hydroxyl group was transformed into a single cyclonucleosidic product, 2,2′-anhydro-3′,5′-di-O-acyluridine. This paper presents a possible mechanism of the reactions, the explanation of observed phenomenon based on semiempirical and density functional theory (DFT) calculations and possible utility of this synthetic pathway.

Geschuetzte Ribonucleoside zur chemischen Synthese von RNA-Sequenzen

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