(1R,3R,4R,7S)-1-(4,4'-Dimethoxytrityloxymethyl)-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
[CAS# 195705-32-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: (1R,3R,4R,7S)-1-(4,4'-Dimethoxytrityloxymethyl)-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• Synonyms: 1-[(1R,3R,4R,7S)-1-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-3-yl]pyrimidine-2,4-dione
• Molecular Formula: C₃₁H₃₀N₂O₈
• Molecular Weight: 558.58
• CAS Registry Number: 195705-32-9
• SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@]45CO[C@H]([C@@H]4O)[C@@H](O5)N6C=CC(=O)NC6=O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

(1R,3R,4R,7S)-1-(4,4'-Dimethoxytrityloxymethyl)-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane is a complex organic compound that combines a bicyclic structure with functional groups that enhance its reactivity and versatility. This compound is part of a family of molecules with applications in the fields of medicinal chemistry, organic synthesis, and nucleic acid research. The structure of this compound is characterized by a bicyclic ring system, a hydroxyl group, a uracil-1-yl group, and a dimethoxytrityloxymethyl group, which imparts significant potential for its role in chemical synthesis and biological interactions.

The discovery of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane likely stems from research efforts focused on the development of novel nucleoside analogs or intermediates for synthetic biology and pharmaceutical development. The inclusion of a uracil moiety suggests its potential use in RNA or DNA-related applications, where uracil is a key nucleobase. This compound may have been designed as part of efforts to develop more efficient methods for manipulating nucleic acids or creating specialized therapeutics.

In the field of medicinal chemistry, this compound’s structure positions it as a potential candidate for the development of nucleotide-based drugs. The incorporation of uracil and the bicyclic structure can be leveraged to enhance interactions with enzymes or other molecular targets involved in cellular processes, including RNA replication or DNA transcription. The hydroxyl group and dimethoxytrityloxymethyl group further provide functional handles for the modification or conjugation of other bioactive molecules, which could improve the drug's efficacy or pharmacokinetic properties. This type of compound could be used in the design of antiviral or anticancer agents, where interference with nucleic acid metabolism is a key therapeutic strategy.

The compound's potential as an intermediate in chemical synthesis is also notable. The presence of the bicyclic ring system and multiple functional groups, such as hydroxyl and trityl moieties, makes this molecule a useful scaffold for building more complex molecules. It could serve as a key intermediate in the synthesis of other biologically active compounds, especially those involved in nucleic acid chemistry. Additionally, the dimethoxytrityl group is commonly employed in protecting group strategies for the synthesis of oligonucleotides and other sensitive biomolecules, making this compound particularly valuable in the field of synthetic organic chemistry.

In conclusion, (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane represents a significant building block in the fields of medicinal chemistry, nucleic acid research, and organic synthesis. Its unique structure and functional groups make it a versatile compound for drug development, particularly in the design of nucleotide-based therapies, as well as a valuable intermediate in the synthesis of complex bioactive molecules.

References

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