CAS 102147-76-2

5′-O-[(1,1-Dimethylethyl)dimethylsilyl]-2′,3′-O-(1-methylethylidene)uridine

Description:

5′-O-[(1,1-Dimethylethyl)dimethylsilyl]-2′,3′-O-(1-methylethylidene)uridine is a modified nucleoside that features a uridine base with specific protective groups. This compound is characterized by the presence of a dimethylsilyl group, which enhances its stability and solubility, making it useful in various biochemical applications. The 1-methylethylidene group provides additional steric hindrance, which can influence the reactivity and interaction of the nucleoside with enzymes and other biological molecules. Such modifications are often employed to improve the pharmacokinetic properties of nucleosides, potentially increasing their resistance to nucleases and enhancing their therapeutic efficacy. The compound is typically used in research settings, particularly in studies involving RNA synthesis and modification, as well as in the development of antiviral agents and other therapeutic applications. Its unique structural features make it a valuable tool in the field of nucleic acid chemistry and molecular biology.

Formula: C₁₈H₃₀N₂O₆Si

InChI: InChI=1S/C18H30N2O6Si/c1-17(2,3)27(6,7)23-10-11-13-14(26-18(4,5)25-13)15(24-11)20-9-8-12(21)19-16(20)22/h8-9,11,13-15H,10H2,1-7H3,(H,19,21,22)/t11-,13-,14-,15-/m1/s1

InChI key: InChIKey=RUTBPSQCGJYSTC-NMFUWQPSSA-N

SMILES: C(O[Si](C(C)(C)C)(C)C)[C@@H]1[C@@]2([C@]([C@@H](O1)N3C(=O)NC(=O)C=C3)(OC(C)(C)O2)[H])[H]

Synonyms:

• 5′-O-[(1,1-Dimethylethyl)dimethylsilyl]-2′,3′-O-(1-methylethylidene)uridine
• Uridine, 5′-O-[(1,1-dimethylethyl)dimethylsilyl]-2′,3′-O-(1-methylethylidene)-
• Furo[3,4-d]-1,3-dioxole, uridine deriv.

5’-O-tert-Butyldimethylsilyl-2’,3’-O-isopropylideneuridinefuro[3,4-d]-1,3-dioxole

CAS: 102147-76-2

5’-O-tert-Butyldimethylsilyl-2’,3’-O-isopropylideneuridinefuro[3,4-d]-1,3-dioxole (TBDMS) is a novel antiviral and anticancer drug. TBDMS is a monophosphate nucleotide analog that binds to the viral RNA polymerase enzyme and blocks the synthesis of viral RNA. TBDMS has been shown to be active against herpes simplex virus type 1 (HSV) in vitro and in vivo with no toxicity to normal cells. It also has an inhibitory effect on myeloid leukemia cells. TBDMS is not active against human DNA polymerase α or β, which are involved in DNA replication.
TBDMS is a high purity product with high quality and good solubility in water. It is soluble in DMSO at a concentration of 0.5 mg/mL at room

Formula: C₁₈H₃₀N₂O₆Si

Purity: Min. 95%

Molecular weight: 398.53 g/mol

Ref: 3D-ND181575