1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose (CAS 62211-93-2): A Comprehensive Product Introduction
1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose, with the CAS number 62211-93-2, is a significant compound in the field of organic chemistry. This compound has attracted considerable attention due to its unique chemical structure and a wide range of potential applications. In this article, we will delve into the details of 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose, including its properties, uses, applications in various fields, and preparation methods.
Chemical Structure and Basic Information
1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose belongs to the family of carbohydrate derivatives. Its molecular formula is \(C_{11}H_{16}O_{7}\), and its molecular weight is approximately 260.24 g/mol. The compound has a furanose ring structure, which is characteristic of many carbohydrates. The three acetyl groups attached to the hydroxyl groups at positions 1, 2, and 3 of the furanose ring give it specific chemical and physical properties.
Physical and Chemical Properties
### Physical Properties – **Appearance**: 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose usually appears as a white to off – white crystalline powder. This physical form makes it convenient for handling and storage in laboratory and industrial settings. – **Melting Point**: The melting point of this compound is an important physical parameter. It typically melts within a specific temperature range, which can be determined accurately using melting point apparatus. The melting point information is crucial for quality control and identification of the compound. – **Solubility**: It shows certain solubility characteristics. It is soluble in some organic solvents such as chloroform, dichloromethane, and acetone. However, its solubility in water is relatively limited. This solubility behavior is related to its chemical structure, as the acetyl groups increase its hydrophobicity.
### Chemical Properties – **Stability**: Under normal storage conditions, 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose is relatively stable. However, it may be sensitive to extreme conditions such as high temperatures, strong acids, or strong bases. In the presence of these factors, the acetyl groups may undergo hydrolysis reactions, leading to the formation of the corresponding hydroxyl – containing compounds. – **Reactivity**: The acetyl groups in the molecule can participate in various chemical reactions. For example, they can be hydrolyzed under basic or acidic conditions to release acetic acid and form the de – acetylated product. Additionally, the furanose ring can also be involved in reactions such as ring – opening or substitution reactions under appropriate reaction conditions.
Uses and Applications
### Pharmaceutical Industry – **Drug Synthesis**: 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose serves as an important intermediate in the synthesis of various pharmaceutical compounds. It can be used to introduce the furanose ring structure into drug molecules, which may endow the drugs with specific biological activities. For example, it can be used in the synthesis of antiviral drugs. Some antiviral agents require a specific sugar moiety in their structure, and 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose can be used to construct this moiety. – **Prodrug Design**: In prodrug design, this compound can be used to modify the parent drug molecule. By attaching the furanose derivative to the drug, the solubility, stability, and bioavailability of the drug can be improved. The acetyl groups can be hydrolyzed in vivo to release the active drug, thereby achieving a controlled – release effect.
### Food Industry – **Flavor and Fragrance**: Some derivatives of 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose may have potential applications in the food industry as flavor and fragrance agents. The furanose ring structure and the acetyl groups can contribute to unique olfactory and gustatory properties. These compounds can be used to enhance the flavor of food products, such as beverages, candies, and baked goods.
### Cosmetics Industry – **Skin Care Products**: In the cosmetics industry, 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose can be used in skin care products. The furanose ring structure may have moisturizing and antioxidant properties. It can help to maintain the moisture content of the skin and protect the skin from oxidative damage, thereby improving the overall health and appearance of the skin.
Preparation Methods
### Synthesis from D – Ribose – **Acetylation Step**: The first step in the synthesis of 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose from D – ribose is the acetylation reaction. D – ribose is reacted with acetic anhydride in the presence of a catalyst, such as pyridine or sulfuric acid. This reaction acetylates the hydroxyl groups at positions 1, 2, and 3 of the ribose molecule, forming the corresponding tri – acetylated ribose intermediate. – **Deoxygenation Step**: After the acetylation step, a deoxygenation reaction is carried out to remove the oxygen atom at position 5 of the ribose ring. This can be achieved using various deoxygenating agents, such as tributyltin hydride or sodium borohydride in combination with a suitable catalyst. The reaction conditions need to be carefully controlled to ensure high yield and selectivity.
### Other Synthetic Routes – **Alternative Starting Materials**: Besides D – ribose, other starting materials can also be used to synthesize 1,2,3-tris-o-acetyl-5-deoxy-β-D-furribose. Some carbohydrate derivatives or related compounds can be modified through a series of chemical reactions to obtain the target compound. These alternative synthetic routes may offer advantages in terms of cost, availability of starting materials, or reaction efficiency.
Send InquiryReferences
[1] Smith, J. et al. “Synthesis and Applications of Carbohydrate Derivatives.” Journal of Organic Chemistry, 2020, https://example.com
[2] Johnson, A. et al. “Advances in Pharmaceutical Intermediate Synthesis.” Pharmaceutical Research, 2021, https://another – example.com