Description

N4-Acetyl-2′-O-tert-butyldimethylsilylcytidine (CAS No. 401812-97-3) is a high-purity, chemically modified nucleoside derivative designed for advanced research applications in nucleic acid chemistry and oligonucleotide synthesis. With the molecular formula C₁₇H₂₉N₃O₆Si, this compound features a tert-butyldimethylsilyl (TBDMS) protecting group at the 2′-hydroxyl position and an acetyl group at the N4 position of cytidine, enhancing its stability and utility in solid-phase RNA synthesis. Its IUPAC name, N-[1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide, reflects its precise stereochemistry and functionalization. Ideal for researchers developing modified oligonucleotides, this product is rigorously characterized by HPLC, NMR, and mass spectrometry to ensure ≥95% purity. Store under inert conditions at -20°C for optimal stability.

Properties

• CAS Number: 401812-97-3
• Complexity: 658
• IUPAC Name: N-[1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]acetamide
• InChI: InChI=1S/C17H29N3O6Si/c1-10(22)18-12-7-8-20(16(24)19-12)15-14(13(23)11(9-21)25-15)26-27(5,6)17(2,3)4/h7-8,11,13-15,21,23H,9H2,1-6H3,(H,18,19,22,24)/t11-,13-,14-,15-/m1/s1
• InChI Key: FFPMJMDVFALXLQ-NMFUWQPSSA-N
• Exact Mass: 399.18256219
• Molecular Formula: C17H29N3O6Si
• Molecular Weight: 399.5
• SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O[Si](C)(C)C(C)(C)C
• Topological: 121
• Monoisotopic Mass: 399.18256219
• Synonyms: 401812-97-3, N4-Acetyl-2′-O-tert-butyldimethylsilylcytidine, N-(1-((2R,3R,4R,5R)-3-((tert-Butyldimethylsilyl)oxy)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide, SCHEMBL6396735, NA71488, AC-32351, N-[1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide, G89828

Application

N4-Acetyl-2′-O-tert-butyldimethylsilylcytidine is a critical intermediate in the synthesis of modified RNA oligonucleotides, particularly for structural studies and therapeutic applications. The TBDMS group protects the 2′-OH during phosphoramidite-based RNA synthesis, while the N4-acetyl modification enhances nucleoside stability. This compound is widely used in antisense technology, siRNA design, and CRISPR guide RNA production. Its compatibility with automated synthesizers makes it valuable for high-throughput research.

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