Description

2′,3′,5′-tri-O-acetyladenosine (CAS No. 7387-57-7) is a highly purified acetylated derivative of adenosine, extensively utilized in biochemical and pharmaceutical research. With the molecular formula C₁₆H₁₉N₅O₇, this compound is characterized by its IUPAC name [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate. It serves as a critical intermediate in nucleoside synthesis, protecting the hydroxyl groups of adenosine during chemical modifications. The product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring optimal performance in sensitive applications. Suitable for use in oligonucleotide synthesis, prodrug development, and enzymatic studies, it is packaged under inert conditions to guarantee stability and longevity.

Properties

• CAS Number: 7387-57-7
• Complexity: 620
• IUPAC Name: [(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methyl acetate
• InChI: InChI=1S/C16H19N5O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3,(H2,17,18,19)/t10-,12-,13-,16-/m1/s1
• InChI Key: GCVZNVTXNUTBFB-XNIJJKJLSA-N
• Exact Mass: 393.12844796
• Molecular Formula: C16H19N5O7
• Molecular Weight: 393.35
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)OC(=O)C)OC(=O)C
• Topological: 158
• Monoisotopic Mass: 393.12844796
• Synonyms: 7387-57-7, 2′,3′,5′-Tri-O-acetyladenosine, Adenosine, 2′,3′,5′-triacetate, NSC 76766, (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate, 2′,3′,5′-Tri-O-acetyl-D-adenosine, MFCD00057001, [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate, Tri-O-acetyladenosine, 2′,3′,5′-Tri-O-acetyl adenosine, Adenosine 2′,3′,5′-Triacetate, C16H19N5O7, SCHEMBL4425824, GCVZNVTXNUTBFB-XNIJJKJLSA-N, 2′,3′,5′-TRI-O-Acetyadenosine, AKOS004903253, DS-8003, NT04548, AC-32263, DB-019682, A51106, [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)oxolan-2-yl]methyl acetate, (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate

Application

2′,3′,5′-tri-O-acetyladenosine is widely employed as a protected nucleoside precursor in the synthesis of modified oligonucleotides and antiviral prodrugs. Researchers leverage its acetylated groups to facilitate selective glycosylation reactions in carbohydrate chemistry. Additionally, it serves as a key substrate in enzymatic assays to study adenosine-metabolizing enzymes such as kinases and deacetylases.

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