14215-97-5

Basic information

• Product Name: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE
• Synonyms: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE;1-ACETYL-2,3,5-TRIBENZOYL-3-D-RIBOFURANOSIDE;TRI-O-BENZOYL-1-O-ACETYL-D-RIBOFURANOSE;1-O-Acetyl-2,3,5-tri-0-benzoyl-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoylribose;1-O-Acetyl-2,3,5-tri-O-benzoyl-α,β-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoyl-alpha,beta-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoyl-α,β-D-ribofuranose
• CAS NO: 14215-97-5
• Molecular Formula: C₂₈H₂₄O₉
• Molecular Weight: 504.48
• Product Categories: Carbohydrates & Derivatives;Inhibitors
• Mol File: 14215-97-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 126-127 °C
• Boiling Point: 621.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Refractive Index: 1.61
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE(14215-97-5)
• EPA Substance Registry System: 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE(14215-97-5)

Safety Data

• Hazardous Substances Data: 14215-97-5(Hazardous Substances Data)

Usage

Uses

An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion

InChI:InChI=1/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23+,24+,28-/m1/s1

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 75-36-5 acetyl chloride 
• 79439-66-0 carboxymethyl-1 methyl-2 N-acetyl-2 (dihydroxy-3,4 phenyl)-3 alanine 
• 39740-33-5 carboxymethyl-1 N-acetyl-2 (dihydroxy-3,4 phenyl)-3 alanine 
• 555-30-6 methyldopa 
• 108-24-7 acetic anhydride 
• 171866-28-7 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose 
• 13039-67-3 (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 609-06-3 L-xylose 
• 1173695-22-1 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose 
• 64-19-7 acetic acid 
• 24259-59-4 L-ribose 
• 98-88-4 benzoyl chloride 
• 69350-76-1 methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside 

Downstream Products

• 173987-28-5 7-amino-5-ethylthio-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazolo<4,5-d>pyrimidine 
• 173987-25-2 2-ethylthio-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine 
• 23392-16-7 5-nitrouridine 2',3',5'-tri-O-benzoate 
• 171866-30-1 1,3,5-Tri-O-benzoyl-α-L-ribofuranose 
• 83866-20-0 C₃₆H₂₉N₃O₈ 
• 178550-90-8 2',3',5'-tri-O-benzoyl-5-benzyluridine 
• 192133-14-5 C₃₂H₂₆O₇Se 
• 862543-11-1 9-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-2-chloro-6-(4-piperonylpiperazin-1-yl)purine 
• 862543-12-2 9-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-2-piperidino-6-(4-phenylpiperazin-1-yl)purine 
• 866826-70-2 4-methyl-5-nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyridin-2-one 
• 237060-98-9 2',3',5'-tri-O-benzoyl-5-methyl-L-uridine 
• 166542-53-6 <8-14C>-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloropurine 
• 106577-76-8 1-(2',3',5'-tri-O-benzoyl-α-D-arbinofuranosyl)cycloheptapyrrol-2(1H)-one 
• 106577-78-0 3-(2',3',5'-tri-O-benzoyl-β-D-arbinofuranosyl)cycloheptapyrrol-2(1H)-one 

Relevant articles and documents

L-nucleoside compounds and application thereof

The invention discloses L-nucleoside compounds having the structure characteristic represented by the formula (I) or pharmaceutically acceptable salts thereof, and belongs to the technical field of pharmaceutical chemistry. The compounds can inhibit the activity of RNA viral polymerase, so the compounds can be used as potential drugs for prevention and treatment of infection of RNA viruses such as HCV, influenza virus, HRV (rhinovirus), RSV, Ebola virus, dengue virus, intestinal virus and the like.

Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides

The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-Lribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac + as the catalytically active species was clarified, proving that the anomerization of the acylated methyl furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated methyl furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage.

METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE

An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.