3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid
[CAS# 119736-16-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid
• Synonyms: 4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid
• Molecular Formula: C₁₃H₁₀O₅
• Molecular Weight: 246.22
• CAS Registry Number: 119736-16-2
• SMILES: C1=CC=C(C=C1)COC2=C(OC=CC2=O)C(=O)O

Properties

• Solubility: Slightly soluble (1.1 g/L) (25 °C), Calc.^*
• Density: 1.39±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.616, Calc.^*
• Boiling Point: 487.5±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 192.6±22.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid is a synthetic organic compound that belongs to the class of pyran derivatives. It is notable for its unique chemical structure, featuring a benzyl group attached to the oxygen atom of the pyran ring, as well as a carboxylic acid functional group. This compound has garnered attention for its potential applications in various fields, particularly in medicinal chemistry and organic synthesis. The discovery and development of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid are linked to the growing interest in the synthesis of pyran-based compounds, which are known for their biological activities.

The initial discovery of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid is often associated with the increasing research into pyran derivatives in the late 20th century. Pyran rings, due to their versatile reactivity, are present in many natural products, and their derivatives have been shown to exhibit a wide range of pharmacological effects. These include antimicrobial, anticancer, and anti-inflammatory activities. The incorporation of a benzyloxy group into the pyran structure in 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid further enhances the compound’s potential biological activities, making it a subject of considerable interest in drug discovery.

The synthesis of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid typically involves the reaction of appropriate starting materials such as benzyloxy compounds with pyran-2-carboxylic acid derivatives under controlled conditions. Several synthetic routes have been developed, with the most common approach being the use of electrophilic aromatic substitution to introduce the benzyloxy group onto the pyran ring. This method is widely employed because of its efficiency and ability to provide high yields. In addition, the synthesis can be modified to optimize the selectivity and functionalization of the pyran ring, depending on the desired final product.

The primary applications of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid lie in the fields of medicinal chemistry and organic synthesis. The compound has shown promise as a building block for the synthesis of more complex molecules with biological activity. For example, derivatives of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid have been explored for their potential anticancer and antimicrobial effects. The presence of both the benzyloxy and carboxylic acid groups makes this compound an ideal candidate for further modification into molecules with enhanced pharmacological profiles. Additionally, its potential for use in the development of enzyme inhibitors and other bioactive agents adds to its importance in drug development.

In conclusion, 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid represents a valuable compound in the realm of synthetic organic chemistry and medicinal research. Its synthesis, applications, and potential for further development make it an interesting subject for future studies aimed at the creation of novel therapeutic agents.

References

2016. Development of Synthetic Routes to Dolutegravir. Synthesis of Heterocycles in Contemporary Medicinal Chemistry.
DOI: 10.1007/7081_2016_200

2019. Synthesis of Dolutegravir. Synfacts.
DOI: 10.1055/s-0039-1690465

2014. Dolutegravir. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0184