Description
5′-O-(4,4-Dimethoxytrityl)-thymidine-3′-succinate, TEA salt (CAS No. 402944-22-3) is a high-purity, synthetic nucleoside derivative widely used in oligonucleotide synthesis and pharmaceutical research. This compound features a 5′-O-DMT (4,4′-dimethoxytrityl) protecting group, a 3′-succinate linker, and is supplied as a triethylammonium (TEA) salt for enhanced solubility and stability. With the molecular formula C41H51N3O10, it is a critical intermediate in solid-phase DNA/RNA synthesis, enabling the controlled elongation of oligonucleotide chains. Ideal for researchers, this product is rigorously tested by HPLC and NMR to ensure ≥95% purity, making it suitable for demanding applications in genomics, diagnostics, and therapeutic development. Store desiccated at -20°C to maintain optimal performance.
Properties
- CAS Number: 402944-22-3
- Complexity: 1140
- IUPAC Name: 4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl]oxy-4-oxo-butanoic acid;N,N-diethylethanamine
- InChI: InChI=1S/C35H36N2O10.C6H15N/c1-22-20-37(34(42)36-33(22)41)30-19-28(47-32(40)18-17-31(38)39)29(46-30)21-45-35(23-7-5-4-6-8-23,24-9-13-26(43-2)14-10-24)25-11-15-27(44-3)16-12-25;1-4-7(5-2)6-3/h4-16,20,28-30H,17-19,21H2,1-3H3,(H,38,39)(H,36,41,42);4-6H2,1-3H3/t28-,29+,30+;/m0./s1
- InChI Key: FOWSKALJTKBTQC-PMGSZYTFSA-N
- Exact Mass: 745.35744483
- Molecular Formula: C41H51N3O10
- Molecular Weight: 745.9
- SMILES: CCN(CC)CC.CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OC(=O)CCC(=O)O
- Topological: 153
- Monoisotopic Mass: 745.35744483
- Synonyms: 402944-22-3, 5′-O-(4,4-Dimethoxytrityl)-thymidine-3′-succinate, TEA salt, 933-444-7, 5′-O-Dmt-thymidine 3′-o-succinate triethylammonium salt, 5′-O-(4,4′-dimethoxytrityl)-thymidine-3′-O-succinic acid triethylammonium salt, MFCD12912408, AT41610, ND08490, 5′-O-Dmt-thymidine3′-o-succinatetriethylammoniumsalt, 5′-O-DMT-D-thymidine 3′-O-succinate triethylamine salt, 5′-O-(4,4′-dimethoxytrityl)-thymidine-3′-O-succinic acid triethylammonium salt, min. 98%, 4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-4-oxobutanoic acid;N,N-diethylethanamine
Application
This compound is primarily used as a building block in oligonucleotide synthesis, particularly in the automated solid-phase synthesis of DNA/RNA sequences. The DMT group protects the 5′-hydroxyl during chain elongation, while the 3′-succinate linker facilitates covalent attachment to solid supports (e.g., CPG or polystyrene resins). Its TEA salt form improves solubility in organic solvents like acetonitrile, essential for phosphoramidite chemistry. Applications include antisense drug development, PCR primer synthesis, and probe design for molecular diagnostics.
Safety and Hazards
GHS Hazard Statements
- H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
- H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
- H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statements
- P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Acute Tox. 4 (100%)
- Acute Tox. 4 (100%)
- Skin Irrit. 2 (100%)
- Eye Irrit. 2 (100%)
- Acute Tox. 4 (100%)
- STOT SE 3 (100%)
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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.
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