21618-67-7

Basic information

• Product Name: 5-(TRIFLUOROMETHYL)-URIDINE
• Synonyms: 5-(TRIFLUOROMETHYL)-URIDINE;500Mg,1g
• CAS NO: 21618-67-7
• Molecular Formula: C₁₀H₁₁F₃N₂O₆
• Molecular Weight: 312.2
• Mol File: 21618-67-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.765g/cm³
• Refractive Index: 1.563
• PKA: 7.75±0.10(Predicted)
• CAS DataBase Reference: 5-(TRIFLUOROMETHYL)-URIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(TRIFLUOROMETHYL)-URIDINE(21618-67-7)
• EPA Substance Registry System: 5-(TRIFLUOROMETHYL)-URIDINE(21618-67-7)

Safety Data

• Hazardous Substances Data: 21618-67-7(Hazardous Substances Data)

Usage

Uses

5-(Trifluoromethyl)uridine is an analog of Uridine (U829910) and used as a reagent in the synthesis of β-D-arabinofuranosyl and deoxyfluoro-β-D-ribofuranosyl pyrimidine nucleoside analogs which exhibit antituberculosis activity against Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium in vitro.

InChI:InChI=1/C10H11F3N2O6/c11-10(12,13)3-1-15(9(20)14-7(3)19)8-6(18)5(17)4(2-16)21-8/h1,4-6,8,16-18H,2H2,(H,14,19,20)/t4-,5-,6-,8-/m1/s1

Upstream product

• 76513-97-8 5-(trifluoromethyl)-2',5'-di-O-trityluridine 
• 2926-29-6 Langlois reagent 
• 58-96-8 uridine 
• 65499-41-4 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate 
• 40554-98-1 [(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate 
• 54-20-6 5-trifluoromethyluracil 
• 50-69-1 D-ribose 
• 2314-97-8 iodotrifluoromethane 
• 76513-96-7 2',5'-di-O-trityl-5-iodouridine 

Downstream Products

• 70-00-8 2'-deoxy-5-trifluoromethyluridine 

Relevant articles and documents

Method for preparing trifluridine

The invention discloses a method for preparing trifluridine. The method comprises the following steps of performing halogenation on ribose fully protected by hydroxyl, performing condensation on the halogenated ribose and 5-(trifluoromethyl)uracil, performing deprotection to generate an intermediate namely 5-trifluoromethyl uridine, and then performing dehydrating, halogenation and a reduction reaction so as to obtain the trifluridine. According to the method disclosed by the invention, the fully protected ribose is used as a raw material, so that the cost of raw materials can be notably reduced; besides, in the condensation reaction process of the ribose protected by 2-site acyl groups, due to effects of neighboring group participation, the beta-stereoselectivity of the condensation reaction is notably increased; the 5-(trifluoromethyl)uracil is used as a raw material, and high-toxicity trifluoromethylating reagents are avoided, so that the method is environmentally-friendly; and a compound as shown in a formula VI begins to use continuous operations, separation and purification on the intermediate are not needed, and final products can be directly generated, so that production and operation are greatly convenient, the production efficiency is improved, and the cost of human resources is reduced.

THERMOSTABLE BIOCATALYST COMBINATION FOR NUCLEOSIDE SYNTHESIS

The present invention relates to a transglycosylation method for the preparation of natural and synthetic nucleosides using a uridine phosphorylase (PyNPase, E.C. 2.4.2.3), a purine nucleoside phosphorylase (PNPase, E.C. 2.4.2.1), or a combination thereof. These biocatalysts may be used as such, or by means of host cells transformed with vectors comprising recombinant DNA gene derived from hyperthermophilic archaea and encoding for the PyNPase and PNPase enzymes.

Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected d -Ribose

New, improved methods to access nucleosides are of general interest not only to organic chemists but to the greater scientific community as a whole due their key implications in life and disease. Current synthetic methods involve multistep procedures employing protected sugars in the glycosylation of nucleobases. Using modified Mitsunobu conditions, we report on the first direct glycosylation of purine and pyrimidine nucleobases with unprotected d-ribose to provide β-pyranosyl nucleosides and a one-pot strategy to yield β-furanosides from the heterocycle and 5-O-monoprotected d-ribose.