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Description
2,2'-O-Cyclouridine (TCI C2208), commonly known as 2,2'-anhydrouridine, is a heterocyclic building block derived from uridine in which a bridging bond links the oxygen atom at the 2' position of the ribose sugar to position 2 of the pyrimidine ring. This bridge is the very core of its usefulness in the laboratory, because the anhydro ring is strained and therefore opened very readily by nucleophiles. As a consequence, the compound serves as a classical synthetic gateway for converting inexpensive uridine into a wide range of 2'-modified nucleosides that are considerably more difficult to obtain by other routes.
The characteristic that makes it the preferred choice is the selectivity of its reactions. Opening of the anhydro ring by fluoride sources, azides, halides, or other nucleophiles proceeds with inversion of configuration, thereby delivering products of arabino configuration or 2'-substituted derivatives with controlled stereochemistry. This approach spares researchers the repeated, time-consuming protection and deprotection steps that alternative routes demand. In addition, the compound is a solid that is relatively easy to handle and weigh out, and it is supplied at the consistent TCI reagent grade, making it well suited to multi-step syntheses that demand high reproducibility.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on nucleoside and nucleotide chemistry, in medicinal chemistry programmes exploring antiviral and anticancer scaffolds, and in postgraduate research where modified nucleosides must be prepared on a laboratory scale. Because it is a stable, easily weighed solid of consistent reagent grade, it fits well into shared synthetic laboratories where several researchers run multi-step sequences and require results that can be repeated between batches and between operators.
Laboratory Applications
- Synthesis of 2'-modified nucleosides: the strained anhydro bridge is opened directly by nucleophiles, converting inexpensive uridine into 2'-substituted analogues that are otherwise difficult to access.
- Preparation of arabino-configured nucleosides: ring opening proceeds with inversion of configuration at the 2' position, giving arabino products with predictable and controlled stereochemistry.
- Introduction of 2'-fluoro substituents: fluoride sources open the anhydro ring cleanly, providing a classical and direct route to fluorinated nucleoside building blocks for further elaboration.
- Preparation of 2'-azido and 2'-halo derivatives: azide and halide nucleophiles attack the strained ring selectively, delivering functionalised intermediates suitable for subsequent transformation.
- Multi-step medicinal chemistry sequences: consistent TCI reagent grade and the avoidance of repeated protection–deprotection steps support reproducible results across extended synthetic routes.
Specifications
- Brand: TCI
- CAS number: 3736-77-4
- Product code: C2208
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Physical form: solid, relatively easy to handle and weigh
- Pack sizes: please refer to the packaging options listed for this catalogue item
- Storage: keep the container tightly closed in a cool, dry place; follow the manufacturer's label and safety data sheet
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, well-ventilated place away from moisture, direct sunlight, and incompatible chemicals, following the storage conditions stated on the manufacturer's label and safety data sheet. Suitable containers are the original amber or opaque chemical bottles with sealing caps; where material is transferred, use clean, dry glass vessels that can be closed securely and are clearly labelled. Handle the solid in a fume hood, wear a laboratory coat, safety glasses, and chemical-resistant gloves, and avoid generating or inhaling dust while weighing. Close the container promptly after use to limit moisture uptake, and dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
