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

• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 108-24-7 acetic anhydride 
• 10323-20-3 D-Arabinose 
• 108-05-4 vinyl acetate 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 28697-53-2 D-arabinopyranose 
• 10257-32-6 D-ribose 
• 50-69-1 D-ribose 
• 146572-26-1 Acetic acid (2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 37077-80-8 2,3,5-tri-O-acetyl-1-O-methyl-β-D-ribofuranose 
• 532-20-7 D-Ribose 
• 52554-28-6 (2R,3R,4R)-2-(acetoxymethyl)-5-methoxytetrahydrofuran-3,4-diyl diacetate 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 

Downstream Products

• 121524-02-5 phenyl-(tri-O-acetyl-1-thio-ξ-D-riboside) 
• 52544-88-4 phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside 
• 14528-15-5 6-azacytidine 
• 64691-28-7 Phenyl 1-thio-β-D-ribofuranoside 
• 220588-06-7 phenyl 1-seleno-β-D-ribofuranoside 
• 220587-60-0 phenyl 1-seleno-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranoside 
• 262421-85-2 (2S,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-phenylsulfanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 262421-86-3 (2S,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(4-methoxy-phenylsulfanyl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 57198-04-6 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester 
• 1038412-57-5 C₁₈H₂₁BrO₈ 
• 1038412-58-6 C₁₈H₂₁IO₈ 
• 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 

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.

Mild Palladium-Catalyzed Cyanation of Unprotected 2-Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2-Glycoanalogues

Access to unprotected 2-cyano-glycals via a mild palladium-catalyzed cyanation of protecting groups-free 2-iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide-type were successfully obtained in good to excellent yields. These unprotected 2-cyano-glycal scaffolds were successfully derivatized to different C2-glycoanalogues. (Figure presented.).

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.