CAS 54925-65-4

5′-O-[(1,1-Dimethylethyl)dimethylsilyl]uridine

Description:

5′-O-[(1,1-Dimethylethyl)dimethylsilyl]uridine is a modified nucleoside that features a uridine base with a silyl protecting group at the 5′ position. This compound is characterized by its unique structure, which includes a uracil base linked to a ribose sugar, with a tert-butyldimethylsilyl (TBDMS) group attached to the hydroxyl group at the 5′ position. The presence of the silyl group enhances the compound's stability and solubility, making it useful in various biochemical applications, particularly in the synthesis of RNA and oligonucleotides. The silyl group serves as a protective moiety, allowing for selective reactions without interfering with the nucleoside's inherent properties. This compound is often utilized in research and development settings, particularly in the fields of molecular biology and synthetic chemistry, where it can facilitate the manipulation of nucleic acids. Its CAS number, 54925-65-4, is a unique identifier that aids in the cataloging and sourcing of this specific chemical substance in scientific literature and databases.

Formula: C₁₅H₂₆N₂O₆Si

InChI: InChI=1S/C15H26N2O6Si/c1-15(2,3)24(4,5)22-8-9-11(19)12(20)13(23-9)17-7-6-10(18)16-14(17)21/h6-7,9,11-13,19-20H,8H2,1-5H3,(H,16,18,21)/t9-,11-,12-,13-/m1/s1

InChI key: InChIKey=IDXWTSSXQWGFCF-OJAKKHQRSA-N

SMILES: O[C@H]1[C@@H](O[C@H](CO[Si](C(C)(C)C)(C)C)[C@H]1O)N2C(=O)NC(=O)C=C2

Synonyms:

• Uridine, 5′-O-[(1,1-dimethylethyl)dimethylsilyl]-
• 5′-O-(tert-Butyldimethylsilyl)uridine
• 5′-O-[(1,1-Dimethylethyl)dimethylsilyl]uridine

5'-O-tert-Butyldimethylsilyluridine

CAS: 54925-65-4

5'-O-tert-Butyldimethylsilyluridine (5'-O-TBDMSU) is a nucleoside that is used in the synthesis of nucleic acid probes. It is selective for the uridine residues in RNA and DNA, which are found at the 5' position. Sodium hydride reacts with this compound to form the corresponding hydroxyl group. This allows for further nucleobase additions or halogen substitutions to be made to the molecule, as well as desilylation reactions. 5'-O-TBDMSU can also be used to synthesize heteroaromatic nucleic acids and nucleotide derivatives.

Formula: C₁₅H₂₆N₂O₆Si

Purity: Min. 98 Area-%

Color and Shape: Powder

Molecular weight: 358.46 g/mol

Ref: 3D-NB09608