2'-FANA Nucleosides
4'-Azido-3'-O-benzoyl-5'-O-(m-chlorobenzoyl)-2'-deoxy-2'-fluoro-beta-D-arabinouridine
Quick view. A protected beta-D-arabinouridine bearing 2'-fluoro, 4'-azido, 3'-O-benzoyl and 5'-O-(3-chlorobenzoyl) substitution, CAS 1333126-30-9. CAS 1333126-30-9. Catalog target purity: By inquiry. Availability: Inquiry only — contact OROGO to confirm current availability.
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Product profile
4'-Azido-3'-O-benzoyl-5'-O-(m-chlorobenzoyl)-2'-deoxy-2'-fluoro-beta-D-arabinouridine is classified as 2'-fana nucleosides (Formula C23H17ClFN5O7; molecular weight 529.86).
4'-Azido-3'-O-benzoyl-5'-O-(m-chlorobenzoyl)-2'-deoxy-2'-fluoro-beta-D-arabinouridine — Protected 4'-azido-2'-fluoro uridine intermediate for pyrimidine nucleoside synthesis research.
For 4'-Azido-3'-O-benzoyl-5'-O-(m-chlorobenzoyl)-2'-deoxy-2'-fluoro-beta-D-arabinouridine, copper-catalyzed, copper-free or inverse-electron-demand click conditions can affect sensitive oligonucleotides differently; residual metal, solvent and purification strategy should be controlled.
Names and search terms
Confirmed or normalized name variants
- 1-[4-Azido-3-O-benzoyl-5-O-(3-chlorobenzoyl)-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)]uracil
Useful catalog search terms
- CAS 1333126-30-9
- PubChem CID 169432469
- TRC-A133315
- InvivoChem V55665
- US 2013/0303747 A1
Physicochemical data
| PubChem CID | 169432469 |
|---|---|
| IUPAC name | [(2R,3R,4S,5R)-2-azido-3-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluorooxolan-2-yl]methyl 3-chlorobenzoate |
| InChI | InChI=1S/C23H17ClFN5O7/c24-15-8-4-7-14(11-15)20(32)35-12-23(28-29-26)18(36-21(33)13-5-2-1-3-6-13)17(25)19(37-23)30-10-9-16(31)27-22(30)34/h1-11,17-19H,12H2,(H,27,31,34)/t17-,18-,19+,23+/m0/s1 |
| InChIKey | ZSOIOSPOWYBGRD-PABYOWBDSA-N |
| SMILES | C1=CC=C(C=C1)C(=O)O[C@H]2[C@@H]([C@@H](O[C@@]2(COC(=O)C3=CC(=CC=C3)Cl)N=[N+]=[N-])N4C=CC(=O)NC4=O)F |
| Nucleobase | Uracil (pyrimidine) |
| Sugar modification | 2'-fluoro and 4'-azido beta-D-arabinofuranosyl |
| Hydroxyl protection | 3'-O-benzoyl and 5'-O-(3-chlorobenzoyl) |
Release documentation
The current specification defines the analytical method and acceptance criteria; the released lot result is reported on the CoA.
Additional HPLC, MS or NMR documentation can be agreed during technical review where available.
Product-specific evaluation notes
Potential advantages
- Click-compatible handles separate oligonucleotide synthesis from late-stage labeling, which helps screen multiple payloads from a common intermediate.
- 2′-fluoro motifs can improve nuclease resistance while preserving RNA-like geometry in many sequence contexts.
Method limitations
- Copper-catalyzed, copper-free or inverse-electron-demand click conditions can affect sensitive oligonucleotides differently; residual metal, solvent and purification strategy should be controlled.
- Coupling, deprotection and biological performance remain sequence- and position-dependent.
These points describe 4'-Azido-3'-O-benzoyl-5'-O-(m-chlorobenzoyl)-2'-deoxy-2'-fluoro-beta-D-arabinouridine or its named chemical feature. Broader product-family guidance is maintained on the category page.
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Product-relevant literature
The publications below discuss named chemistry or a structural feature represented by this product. They provide scientific context only and are not an OROGO lot specification or product-performance claim.
Feature and workflow background
These publications discuss a broader chemistry feature or workflow identified from the catalog name or product family. They are background reading only, not evidence for the exact OROGO product, supplied form, lot specification, availability or performance.
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Technology platforms
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