3180-76-5

Basic information

• Product Name: Uridine, 5-methyl-, 2',3',5'-tribenzoate
• CAS NO: 3180-76-5
• Molecular Formula: C31H26N2O9
• Molecular Weight: 570.555
• Mol File: 3180-76-5.mol
• Article Data: 39

Chemical Properties

• CAS DataBase Reference: Uridine, 5-methyl-, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 5-methyl-, 2',3',5'-tribenzoate(3180-76-5)
• EPA Substance Registry System: Uridine, 5-methyl-, 2',3',5'-tribenzoate(3180-76-5)

Safety Data

• Hazardous Substances Data: 3180-76-5(Hazardous Substances Data)

Usage

General Description

The chemical compound "uridine, 5-methyl-, 2',3',5'-tribenzoate" is a tribenzoate ester derivative of uridine, a nucleoside that is found in RNA. The molecule consists of a uridine base with a 5-methyl group and is esterified with three benzoic acid moieties at the 2', 3', and 5' positions. This modification of uridine confers unique properties to the compound, such as improved stability, solubility, and bioavailability. The 2',3',5'-tribenzoate ester of uridine has been studied for its potential use in pharmacological and biochemical applications, including as a prodrug for targeted delivery of uridine to specific tissues and as a substrate for enzymatic reactions in synthetic biology and biotechnology. Additionally, it may also have uses in research and development within the pharmaceutical industry.

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 2140-61-6 5-methylcytidine 
• 303041-26-1 1-[3-(trifluoromethyl)benzoyl]-2,3,5-tribenzoyl-β-D-ribofuranose 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 613-90-1 benzoyl cyanide 
• 1463-10-1 5-Methyluridine 
• 1055317-41-3 2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate 
• 65-71-4 thymin 
• 1311109-66-6 C₃₉H₃₄O₉ 
• 1824-96-0 methyl ribofuranoside 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 163496-05-7 C₃₃H₂₇N₅O₈ 
• 4336-39-4 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate 
• 173169-09-0 O⁴-2-<(4-cyanophenyl)ethyl>ribosylthymine 
• 173169-10-3 O⁴-2-<(4-nitrophenyl)ethyl>ribosylthymine 
• 173170-13-3 2',3',5'-tri-O-acetyl-O⁴-2-<(4-cyanophenyl)ethyl>ribosylthymine 
• 173169-45-4 O⁴-2-<4-(cyanophenyl)ethyl>-5'-O-(monomethoxytrityl)ribosylthymine 
• 173169-08-9 2',3',5'-tri-O-acetyl-O⁴-(triisopropylbenzenesulfonyl)ribosylthymine 
• 26879-47-0 1-(β-L-ribofuranosyl)thymine 
• 24751-68-6 O^2'_,O3'_,O5'-tribenzoyl-5-bromomethyl-uridine 
• 30414-00-7 5-(hydroxymethyl)uridine 
• 93-89-0 benzoic acid ethyl ester 
• 55-21-0 benzamide 
• 1463-10-1 5-Methyluridine 

Relevant articles and documents

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.

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.