28708-32-9

Basic information

• Product Name: TETRAACETYLRIBOFURANOSE
• Synonyms: TETRACAETATE PENTOFURANOSE;TETRAACETYLRIBOFURANOSE;tetra-O-acetyl-D-ribofuranose;TETRACAETATE PENTOFURAROSE;1-O,2-O,3-O,5-O-Tetraacetyl-D-ribofuranose;D-Ribofuranose tetraacetate;1,2,3,5-tetra-O-acetyl-D-ribofuranose, 1,2,3,5-tetra-O-acetyl-ribofuranose, tetra-O-acetylribofuranose;(3R,4R,5R)-5-(AcetoxyMethyl)tetrahydrofuran-2,3,4-triyl triacetate
• CAS NO: 28708-32-9
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28
• EINECS: 249-174-1
• Mol File: 28708-32-9.mol
• Article Data: 33

Chemical Properties

• Melting Point: 82 °C(Solv: chloroform (67-66-3))
• Boiling Point: 385.624 °C at 760 mmHg
• Flash Point: 168.471 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: TETRAACETYLRIBOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAACETYLRIBOFURANOSE(28708-32-9)
• EPA Substance Registry System: TETRAACETYLRIBOFURANOSE(28708-32-9)

Safety Data

• Hazardous Substances Data: 28708-32-9(Hazardous Substances Data)

Usage

Uses

Tetra-O-acetyl-D-ribofuranose is a useful product for proteomic research.

InChI:InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13?/m1/s1

Upstream product

• 87-72-9 L-(+)-arabinose 
• 108-24-7 acetic anhydride 
• 5328-37-0 L-arabinose 
• 851367-08-3 methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 
• 1355330-54-9 1,2,3,5-tetra-O-tert-butyldimethylsilyl-α-L-arabinofuranose 
• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 28697-53-2 D-arabinopyranose 
• 32453-59-1 (2R,3S,4R,5R)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 10323-20-3 D-Arabinose 
• 108-05-4 vinyl acetate 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 532-20-7 D-Ribose 

Downstream Products

• 121524-02-5 phenyl-(tri-O-acetyl-1-thio-ξ-D-riboside) 
• 15981-63-2 2',3',5'-tri-O-acetylnebularine 
• 15981-64-3 tri-O-acetyl-1-purin-7-yl-β-D-1-deoxy-ribofuranose 
• 1141769-58-5 ethyl 2-(4-chlorophenyl)-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 
• 1141769-57-4 ethyl 2-phenyl-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 
• 119240-35-6 1,2,3-tri-O-acetyl-α-D-ribofuranoside 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 320-67-2 5-azacytidine 
• 1415010-16-0 2,3,5-tri-O-acetyl-1-O-(4-phenylphenyl)-β-D-ribofuranoside 
• 1415009-87-8 2,3,5-tri-O-acetyl-1-O-(4-phenylphenyl)-α-D-ribofuranoside 
• 1415010-19-3 2,3,5-tri-O-acetyl-1-O-(3-methylphenyl)-β-D-ribofuranose 
• 1415009-88-9 C₁₈H₂₂O₈ 
• 1415009-96-9 2,3,5-tri-O-acetyl-1-O-(4-methylphenyl)-β-D-ribofuranose 
• 1415009-89-0 p-methoxyphenyl 2,3,5-tri-O-acetyl-α-D-ribofuranoside 

Relevant articles and documents

First Analog of Pyrimidine Nucleosides with Two D-Ribofuranose Residues

The reaction of 1,3-bis(pent-4-yn-1-yl)-6-methyluracil with 2,3,5-tri-O-acetyl-β-D-ribofuranosyl azide gave 1,3-bis{3-[1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl}-6-methyluracil which was deprotected by treatment with a solution of sodium methoxide in methanol to obtain 1,3-bis{3-[1-(β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl]-6-methyluracil as a first analog of pyrimidine nucleosides containing two D-ribofuranose fragments.

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.