Description
(2R,3S,5R)-5-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS No. 178995-71-6) is a high-purity nucleoside analog designed for advanced biochemical and pharmaceutical research. With the molecular formula C11H11ClIN3O3, this compound features a chlorinated and iodinated pyrrolo[2,3-d]pyrimidine core, coupled with a hydroxymethyl-substituted tetrahydrofuran ring, offering unique reactivity for nucleoside-based studies. Its stereospecific configuration (2R,3S,5R) ensures precise interactions in enzymatic and receptor-binding assays. Ideal for medicinal chemistry, antiviral research, and nucleotide analog development, this compound is supplied with comprehensive analytical data (HPLC, NMR, MS) to guarantee quality and reproducibility. Store under inert conditions at -20°C to maintain stability.
Properties
- CAS Number: 178995-71-6
- Complexity: 340
- IUPAC Name: (2R,3S,5R)-5-(4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
- InChI: InChI=1S/C11H11ClIN3O3/c12-10-9-5(13)2-16(11(9)15-4-14-10)8-1-6(18)7(3-17)19-8/h2,4,6-8,17-18H,1,3H2/t6-,7+,8+/m0/s1
- InChI Key: IBTCDOMWNGACAS-XLPZGREQSA-N
- Exact Mass: 394.95337
- Molecular Formula: C11H11ClIN3O3
- Molecular Weight: 395.58
- SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C2N=CN=C3Cl)I)CO)O
- Topological: 80.4
- Monoisotopic Mass: 394.95337
- Synonyms: 178995-71-6, (2R,3S,5R)-5-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol, (2R,3S,5R)-5-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)oxolan-3-ol, 7H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-iodo-, AKOS025402573, DB-120483
Application
This compound serves as a key intermediate in the synthesis of modified nucleosides for antiviral and anticancer drug discovery. Its halogenated pyrrolopyrimidine structure enables selective cross-coupling reactions in medicinal chemistry. Researchers utilize it to study enzyme inhibition mechanisms, particularly in viral polymerase targeting. It is also valuable for probing nucleotide metabolism and DNA/RNA interaction studies.
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