54618-11-0

Basic information

• Product Name: Uridine, 3',5'-dibenzoate
• Synonyms: 3',5'-Di-O-benzoyluridin;3',5'-O-dibenzoyluridine;O3',O5'-dibenzoyl-uridine;((2R,3S,4R,5R)-3-(BENZOYLOXY)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-4-HYDROXYTETRAHYDROFURAN-2-YL)METHYL BENZOATE
• CAS NO: 54618-11-0
• Molecular Formula: C23H20N2O8
• Molecular Weight: 452.42
• Mol File: 54618-11-0.mol
• Article Data: 8

Chemical Properties

• Density: 1.48±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Uridine, 3',5'-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 3',5'-dibenzoate(54618-11-0)
• EPA Substance Registry System: Uridine, 3',5'-dibenzoate(54618-11-0)

Safety Data

• Hazardous Substances Data: 54618-11-0(Hazardous Substances Data)

Upstream product

• 1748-04-5 tribenzoyl uridine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 73793-15-4 1,3,5-tri-O-benzoyl-2-O-(tert-butyldimethylsilyl)-α-D-ribofuranose 
• 73793-18-7 3',5'-di-O-benzoyl-2'-O-(tert-butyldimethylsilyl)uridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 58-96-8 uridine 
• 31616-01-0 3’,5’-O-benzoyl-2,2’-anhydrouridine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 944476-44-2 C₂₄H₂₂N₂O₈ 
• 944476-43-1 C₂₄H₂₀N₂O₇ 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 1330027-17-2 2'-O-benzyl-3',5'-O-dibenzoyluridine 
• 1330026-92-0 2'-O-trimethylsilyl-3',5'-O-dibenzoyluridine 

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.

A (2 'R) -2' - deoxy -2 '- fluoro -2' - methyl urea glucoside preparation method (by machine translation)

The invention discloses a (2 'R) -2' - deoxy -2 '- fluoro -2' - methyl urea glucoside (type I) synthetic method. Cheap and easily available starting material, through the hydroxyl protection, cyclization, the links such as fluoride, obtains the type I compound. (by machine translation)

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.