Description

beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate (CAS No. 6974-32-9) is a high-purity, synthetic ribofuranose derivative extensively utilized in carbohydrate chemistry and nucleoside synthesis. This compound, with the molecular formula C₂₈H₂₄O₉, features a beta-D-ribofuranose core selectively protected with acetyl and benzoyl groups at the 1-, 2-, 3-, and 5-positions, ensuring optimal reactivity for controlled glycosylation reactions. Its IUPAC name, [(2R,3R,4R,5S)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate, reflects its stereospecific configuration, critical for precise synthetic applications.

Supplied as a white to off-white crystalline powder, this reagent is rigorously tested for purity (typically ≥95% by HPLC or NMR) and stability, making it ideal for sensitive organic transformations. It is packaged under inert conditions to prevent degradation and is compatible with anhydrous reaction environments. Researchers value this compound for its role in constructing complex nucleosides, nucleotides, and glycomimetics, particularly in pharmaceutical and biochemical studies.

Synonyms include 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose and NSC 23349. Store in a cool, dry place (-20°C recommended for long-term stability).

Properties

• CAS Number: 6974-32-9
• Complexity: 793
• IUPAC Name: [(2R,3R,4R,5S)-5-acetoxy-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate
• InChI: InChI=1S/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
• InChI Key: GCZABPLTDYVJMP-CBUXHAPBSA-N
• Exact Mass: 504.14203234
• Molecular Formula: C28H24O9
• Molecular Weight: 504.5
• SMILES: CC(=O)O[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Topological: 114
• Monoisotopic Mass: 504.14203234
• Synonyms: 6974-32-9, 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, .beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate, EINECS 230-220-4, NSC 23349, beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate, DTXSID40884346, 1-Acetyl-2,3,5-tribenzoyl-beta-D-ribofuranose, Acetyl-tribenzoyl-.beta.-d-ribofuranose, 1-Acetyl-2,3,5-tribenzoyl-.beta.-D-ribofuranose, 1-O-Acetyl-2,3,5-O-benzoyl-.beta.-d-ribofuranose, 1-O-Acetyl-2,3,5-tri-O-benzoyl-.beta.-D-ribofuranose, 1-O-Acetyl-2,3,5-tri-O-benzyl-.beta.-D-ribofuranose, DTXCID901023793, Acetyl-tribenzoyl-beta-d-ribofuranose, 1-O-Acetyl-2,3,5-O-benzoyl-beta-d-ribofuranose, 1-O-Acetyl-2,3,5-tri-O-benzyl-beta-D-ribofuranose, 230-220-4, gczabpltdyvjmp-cbuxhapbsa-n, beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, 1-O-Acetyl-2,3,5-tri-O-benzoyl-b-D-ribofuranose, MFCD00005357, (2S,3R,4R,5R)-2-Acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate, NSC-23349, 1-O-Acetyl-2,3,5-tri-O-benzoylpentofuranose #, UL5PL2ZUD2, SCHEMBL308250, 1-ACETYL-2,3,5-TRIBENZOY-B-D-RIBOFURANOSE, 1-O-Acetyl-2,3,5-tri-O-benzoyl-?-D-ribofuranose, Ribofuranose, 1-acetate 2,3,5-tribenzoate, beta-D-, AKOS015889645, AC-4270, CS-W007928, MA05942, [(2R,3R,4R,5S)-5-(acetyloxy)-3,4-bis(benzoyloxy)oxolan-2-yl]methyl benzoate, AS-13409, NS00043809, R0067, F16262, |A-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribose, 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl acetate, beta-D-Ribofuranose,1-acetate 2,3,5-tribenzoate, 1-o-acetyl-2,3,5-tri-o-benzoylbeta-d-ribofuranose, 1-O-Acetyl-2,3,4-tri-O-benzoyl-beta-D-ribofuranose, 1-O-acetyl-2,3,5-tri-O-benzoyl beta-D-ribofuranose, 1-O-Acetyl-2,3,5-tri-O-benzoyl- beta -D-ribofuranose, beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, 98%, Ribofuranose, 1-acetate 2,3,5-tribenzoate, .beta.-D-

Application

This ribofuranose derivative serves as a key intermediate in the synthesis of modified nucleosides for antiviral and anticancer drug development. Its protected hydroxyl groups enable regioselective functionalization, essential for constructing oligonucleotides and mRNA analogs. Researchers also employ it in glycosylation reactions to study enzyme mechanisms or develop carbohydrate-based vaccines. The compound’s stability under anhydrous conditions makes it suitable for organometallic coupling reactions in medicinal chemistry.

Safety and Hazards

GHS Hazard Statements

• Not Classified
• Reported as not meeting GHS hazard criteria by 4 of 4 companies. For more detailed information, please visit ECHA C&L website.

Hazard Classes and Categories

• Not Classified

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