16205-60-0

Basic information

• Product Name: 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide
• Synonyms: 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide
• CAS NO: 16205-60-0
• Molecular Weight: 525.353
• Mol File: 16205-60-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 611.4±55.0 °C(Predicted)
• Density: 1.49±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide(16205-60-0)
• EPA Substance Registry System: 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide(16205-60-0)

Safety Data

• Hazardous Substances Data: 16205-60-0(Hazardous Substances Data)

Usage

General Description

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide is a chemical compound with the molecular formula C26H23BrO7. It is a derivative of ribofuranosyl bromide and is commonly used in organic synthesis and as a reagent in chemical reactions. Its molecular structure consists of a ribofuranosyl group with three benzoyl groups attached to the hydroxyl groups at the 2, 3, and 5 positions. 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide is known for its ability to react with nucleophiles and form various glycosidic bonds, making it useful in the synthesis of nucleosides and nucleotides. Additionally, it is often used in the preparation of carbohydrate-derived compounds for pharmaceutical applications and medicinal chemistry research.

Upstream product

• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 69350-76-1 methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside 

Downstream Products

• 1585182-46-2 N’-(2,3,5-tri-o-benzoyl-β-D-ribofuranosyl)-3-aminocarbonyl-5-ethyl-pyridinium bromide 
• 1234803-65-6 C₄₅H₄₆N₂O₇ 
• 1234803-63-4 C₃₈H₃₄Cl₂N₂O₇ 
• 1234803-60-1 C₃₈H₃₅ClN₂O₇ 
• 1234803-52-1 C₄₈H₄₀N₂O₇ 
• 1234803-64-5 2-spirocyclohexanecyclohexa[2,1-c]-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3-dihydro-1,5-benzodiazepine 

Relevant articles and documents

Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- A nd 2′-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties

The special nucleobase recognition pattern of 5-aza-7-deazaguanine nucleosides makes them valuable for construction of homo purine DNA, silver-mediated base pairs, and expansion of the four letter genetic coding system. To widen the utility of 5-aza-7-deazaguanine nucleosides, side chains were introduced at position-7 of the nucleobase. As key compounds, 7-iodo nucleosides were synthesized. Nucleobase anion glycosylation of the iodo derivative of isobutyrylated 5-aza-7-deazaguanine with the bromo sugar of 2,3,5-tri-O-benzoyl-1-O-acetyl-d-ribofuranose gave the pure β-D anomeric N-9 glycosylation product (67%), whereas one-pot Vorbrüggen conditions gave only 42% of the iodinated nucleoside. The noniodinated nucleoside was formed in 84%. For the synthesis of 2′-deoxyribonucleosides, anion glycosylation performed with Hoffer's 2′-deoxyhalogenose yielded an anomeric mixture (α-D = 33% and β-D = 39%) of 2′-deoxyribonucleosides. Various side chain derivatives were prepared from nonprotected nucleosides by Pd-assisted Sonogashira or Suzuki-Miyaura cross-coupling. Among the functionalized ribonucleosides and anomeric 2′-deoxyribonucleosides, some of them showed strong fluorescence. Benzofuran and pyrene derivatives display high quantum yields in non-aqueous solvents and solvatochromism. Single-crystal X-ray analysis of 7-iodo-5-aza-7-deaza-2′-deoxyguanosine displayed intermolecular iodo-oxygen interactions in the crystal and channels filled with solvent molecules.

Engineering the substrate specificity of ADP-ribosyltransferases for identifying direct protein targets

Adenosine diphosphate ribosyltransferases (ARTDs; ARTD1-17 in humans) are emerging as critical regulators of cell function in both normal physiology and disease. These enzymes transfer the ADP-ribose moiety from its substrate, nicotinamide adenine dinucle

Synthesis of ribonucleosides of 2-thioxopyrido [2,3-d]pyrimidines by phase transfer catalysis and their antimicrobial activity

The ribonucleosides viz; 2-thioxo-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl) pyrido[2,3-d]pyrimidine-4 (1H)-ones have been synthesized via phase transfer ribosylation of 2-thioxo- 3,5,7-trisubstituted pyrido[2,3-d)pyrimidine-4(1H)-ones with 2,3,5-tri-O-benzoyl-β-D- ribofuranosyl bromide in biphasic solvent such as CH2Cl2-50% aqueous NaOH using tetrabutylammonium bromide as phase transfer catalysis (PTC). The synthesized compounds have been characterized by elemental analyses, spectral data and screened for their antimicrobial activity.