7408-41-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide is used as a key intermediate in the synthesis of novel ribonucleosides for their potential antiviral properties. The development of these ribonucleosides aims to provide new treatment options for viral infections, enhancing the arsenal of antiviral medications available to combat various viral diseases.

InChI:InChI=1/C26H21N3O7/c27-29-28-23-22(36-26(32)19-14-8-3-9-15-19)21(35-25(31)18-12-6-2-7-13-18)20(34-23)16-33-24(30)17-10-4-1-5-11-17/h1-15,20-23H,16H2/t20-,21-,22-,23-/m1/s1

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 70832-64-3 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 146916-91-8 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-t-butyl-3H-v-triazolo<4,5-d>pyrimidine 
• 71874-06-1 5-(bromomethyl)-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole 
• 75921-13-0 1-(2',3',5'-Tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazol 
• 75921-18-5 (1R,6R,7R,8S)-3-Phenyl-4,9-dioxa-2-azabicyclo<4.2.1>non-2-en-7,8-diyl-dibenzoat 
• 122087-69-8 N,O³,O⁵-tribenzoyl-α-D-ribofuranosylamine 
• 63621-58-9 N-(N-benzyloxycarbonyl-glycyl)-α-D-ribofuranosylamine 
• 1088232-80-7 N-(N-benzyloxycarbonyl-glycyl)-β-D-ribofuranosylamine 
• 70832-65-4 2,3,5-tri-O-benzoyl-α-D-ribofuranosyl azide 
• 1064666-94-9 2',3',5'-tri-O-benzoyl-1'-deoxy-1'-[4-(4-fluoro-3-methylphenyl)-[1,2,3]triazol-1-yl]ribofuranose 
• 1064667-02-2 2',3',5'-tri-O-benzoyl-1'-deoxy-1'-[5-(4-fluoro-3-methylphenyl)-[1,2,3]triazol-1-yl]ribofuranose 
• 1064666-99-4 2',3',5'-tri-O-benzoyl-1'-deoxy-1'-[4-tert-butyl-[1,2,3]triazol-1-yl]ribofuranose 
• 1064667-07-7 2',3',5'-tri-O-benzoyl-1'-deoxy-1'-[5-tert-butyl-[1,2,3]triazol-1-yl]ribofuranose 
• 1064666-98-3 2',3',5'-tri-O-benzoyl-1'-deoxy-1'-[4-(3-chloropropyl)-[1,2,3]triazol-1-yl]ribofuranose 

Relevant academic research and scientific papers

Click synthesis of N1-(β-D-ribofuranosyl)-C4-(coumarin-4″-yl)-1,2,3-triazoles

A series of eight N1-(β-D-ribofuranosyl)-C4-(coumarin-4′′-yl)-1,2,3-triazoles have been synthesized by Cu(I)-catalyzed click reaction of 1-azido-1-deoxy-2,3,5-tri-O-benzoyl-β-D-ribofuranose with differently substituted 4-ethynylcouma

Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl- / -coumarinyl-1,2,3-triazole

A series of β-D-ribofuranosyl coumarinyl-1,2,3-triazoles have been synthesized by Cu-catalyzed cycloaddition reaction between azidosugar and 7-O-/7-alkynylated coumarins in 62–70% overall yields. The in vitro antimycobacterial activity evaluation of the s

Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones

[Figure not available: see fulltext.] Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine

Synthesis, Antiplatelet Aggregation Activity Evaluation and 3D-QSAR of a Series of Novel 6-Alkylamino(Alkoxyl)-2-Propylthio-8-Azapurine Nucleosides

A series of novel 6-alkylamino(alkoxyl)-2-propylthio-8-azapurine nucleosides were synthesized by an improved route, and the human antiplatelet aggregation activities of these new compounds were evaluated. A self-organizing molecular field analysis method was used to study the three-dimensional quantitative structure–activity relationship of these novel nucleosides. The results of the antiplatelet aggregation activity evaluation and analysis of the self-organizing molecular field analysis models through shape and electrostatic grids may provide a basis for the development of new and potent antiplatelet agents.

[18F]Si-RiboRGD: From design and synthesis to the imaging of αvβ3 integrins in melanoma tumors

The winning combination: A new and promising 18F-labeled RGD derivative has been efficiently prepared by exploiting the advantages of "click" chemistry and a one-step labeling protocol where a silicon-based building blocks was used (see figure). This derivative could be a new starting point for improved visualization of αvβ 3-positive tumors by positron emission tomography.

Probing myo-inositol 1-phosphate synthase with multisubstrate adducts

The synthesis of a series of carbohydrate-nucleotide hybrids, designed to be multisubstrate adducts mimicking myo-inositol 1-phosphate synthase first oxidative transition state, is reported. Their ability to inhibit the synthase has been assessed and resu

Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics

The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogena

Copper catalyzed 1,3-dipolar cycloaddition reaction of azides with N-(2-trifluoroacetylaryl)propargylamines. A mild entry to novel 1,4-disubstituted-[1,2,3]-triazole derivatives

The synthesis of N-(2-trifluoroacetylaryl)propargylamines 10-14 and 17 is presented. The copper(I) catalyzed cycloaddition reaction of these propargylamines (dipolarophiles) with a series of azides (1,3-dipoles) 18-20, 21 and 24 was found to proceed smoothly in dimethylsulfoxide at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]triazole derivatives 26-36 in moderate to good yields.

Studies on the origin of stereoselectivity in the synthesis of 1,2-trans glycofuranosyl azides

The stereoselectivity of the 1,2-trans directed, Lewis acid-catalysed azidation of peracylated furanoses was found to depend on the reactivity of the azide donor (azide nucleophilicity) and the configuration at the anomeric centre relative to the neighbouring 2-O-acyl group. Reactions of 1,2-trans glycosyl esters with highly nucleophilic azide donors, generated from SnCl4 and Me3SiN3, were stereospecific. The results are interpreted in terms of the rapid reaction of the azide species with bicyclic 1,2-acyloxonium (1,2-O-alkyliumdiyl-D-glycofuranose) ions, which were the primarily formed reactive intermediates. When using 1,2-cis glycosyl esters as starting materials the selectivity was reduced (90-94% de); the same is true with 1,2-trans counterparts if less nucleophilic Me3SiN3 in combination with Me3SiOTf catalyst was used. This occurred due to the appearance of the more reactive but less selective oxocarbenium (glycofuranoxonium) ions either as primarily formed reactive intermediates in the former case or after equilibration with acyloxonium ions in the latter case. Protected 1,2-trans β-D-glycofuranosyl azides with ribo, xylo and 3-deoxy-erythro-pento configurations were best prepared from the corresponding glycosyl esters using 0.05 equivalents of SnCl4, i.e., under anomerization-free conditions. Azidation of methyl glycofuranosides proceeds with inferior (80-90% de) and less predictable selectivity irrespective of the starting anomeric configuration. Copyright (C) 2000 Elsevier Science Ltd.

An improved preparation of 2,3,5-tri-O-acyl-β-D-ribofuranosyl azides by the Lewis acid-catalysed reaction of β-D-ribofuranosyl acetates and trimethylsilyl azide: An example of concomitant formation of the α anomer by trimethylsilyl triflate catalysis

An improved synthesis of 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl azide (A) involves the reaction of trimethylsilyl azide in the presence of a Lewis acid with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose rather than the action of sodium azide upon t