Description
1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-2,4(1H,3H)-pyrimidinedione (CAS: 144822-63-9) is a highly specialized nucleoside analog with a molecular formula of C30H29FN2O7. This compound features a modified arabinofuranosyl backbone with a 2-deoxy-2-fluoro substitution and a 5-O-[bis(4-methoxyphenyl)phenylmethyl] (DMT) protecting group, making it a valuable intermediate in oligonucleotide synthesis and pharmaceutical research. Its unique structure is designed for enhanced stability and controlled reactivity in nucleoside-based applications. Suitable for researchers and scientists in medicinal chemistry, molecular biology, and drug development, this product is provided with high purity and rigorous quality control to ensure optimal performance in synthetic workflows.
Properties
- CAS Number: 144822-63-9
- Complexity: 872
- IUPAC Name: 1-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-3-fluoro-4-hydroxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione
- InChI: InChI=1S/C30H29FN2O7/c1-37-22-12-8-20(9-13-22)30(19-6-4-3-5-7-19,21-10-14-23(38-2)15-11-21)39-18-24-27(35)26(31)28(40-24)33-17-16-25(34)32-29(33)36/h3-17,24,26-28,35H,18H2,1-2H3,(H,32,34,36)/t24-,26+,27-,28-/m1/s1
- InChI Key: CSSFZSSZXOCCJB-KCPYNUOSSA-N
- Exact Mass: 548.19587943
- Molecular Formula: C30H29FN2O7
- Molecular Weight: 548.6
- SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H]([C@@H]([C@@H](O4)N5C=CC(=O)NC5=O)F)O
- Topological: 107
- Monoisotopic Mass: 548.19587943
- Synonyms: 144822-63-9, 1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-2,4(1H,3H)-pyrimidinedione, 1-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-fluoro-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione, SCHEMBL17090835, AKOS015909663, AC-32238, DB-215913, F90261, 1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-2,4(1H,3H)-pyrim, 1-{5-O-[bis-(4-Methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-D-arabinofuranosyl}-2,4(1H,3H)-pyrimidinedione
This compound is primarily used as a protected nucleoside intermediate in the synthesis of oligonucleotides, particularly for antisense and siRNA therapeutics. Its 2-fluoro modification enhances binding affinity and nuclease resistance, making it ideal for targeted gene silencing applications. Researchers also employ it in the development of antiviral and anticancer nucleoside analogs due to its structural versatility.
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