Description

3′-O-Acetylthymidine (CAS No. 21090-30-2) is a high-purity nucleoside derivative with the molecular formula C₁₂H₁₆N₂O₆. This compound is a modified thymidine analog featuring an acetyl group at the 3′-position of the ribose sugar, enhancing its stability and utility in nucleic acid research. Widely used in oligonucleotide synthesis, 3′-O-Acetylthymidine serves as a key intermediate for protecting groups in solid-phase DNA/RNA synthesis, ensuring controlled elongation and preventing unwanted side reactions. Its purity (>98% by HPLC) makes it ideal for sensitive biochemical applications, including enzymatic studies, polymerase chain reaction (PCR), and structural biology research. Packaged under inert conditions to ensure stability, this product is suitable for researchers requiring precise and reliable nucleoside modifications.

Properties

• CAS Number: 21090-30-2
• Complexity: 475
• IUPAC Name: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl] acetate
• InChI: InChI=1S/C12H16N2O6/c1-6-4-14(12(18)13-11(6)17)10-3-8(19-7(2)16)9(5-15)20-10/h4,8-10,15H,3,5H2,1-2H3,(H,13,17,18)/t8-,9+,10+/m0/s1
• InChI Key: IRFKBRPHBYCMQU-IVZWLZJFSA-N
• Exact Mass: 284.10083623
• Molecular Formula: C12H16N2O6
• Molecular Weight: 284.26
• SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)OC(=O)C
• Topological: 105
• Monoisotopic Mass: 284.10083623
• Synonyms: 21090-30-2, 3′-O-Acetylthymidine, Thymidine, 3′-acetate, CHEMBL266234, (2R,3S,5R)-2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate, [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate, 3′-O-Acetyl-D-thymidine, C12H16N2O6, MFCD00056059, SCHEMBL265600, 3′-O-Ac-T, SCHEMBL10580671, IRFKBRPHBYCMQU-IVZWLZJFSA-N, BDBM50375420, NA08376, AC-32259, AS-86253, 3 inverted exclamation marka-O-Acetylthymidine, G77712, [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl] acetate

3′-O-Acetylthymidine is primarily used as a protected nucleoside in oligonucleotide synthesis, enabling controlled elongation during automated DNA/RNA assembly. It serves as a precursor for modified nucleotides in structural biology studies, particularly X-ray crystallography and NMR spectroscopy. Researchers also employ it in enzymatic assays to investigate polymerase specificity and nucleotide incorporation kinetics.

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