The Chemical Profile of 1-O-Acetyl-2,3,5-tribenzoyl-beta-D-ribofuranose: Synthesis and Applications
Understanding the intricate details of chemical compounds is fundamental to their successful application in various industries, especially in pharmaceuticals. Beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, also known by its systematic name 1-O-Acetyl-2,3,5-tribenzoyl-beta-D-ribofuranose (CAS 6974-32-9), is a prime example of a chemically sophisticated intermediate with significant utility. This article explores its chemical profile, synthesis routes, and its crucial roles in advanced organic chemistry and pharmaceutical production.
Chemically, beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate is characterized by its specific molecular formula (C28H24O9) and molecular weight (504.48 g/mol). It typically presents as a white to off-white crystalline powder. Its properties include a melting point in the range of 128-130 °C and limited solubility in common organic solvents like methanol. The optical activity, often measured as [α]20/D +24.3° in pyridine, is a key characteristic that confirms its stereochemical integrity. These physical and chemical properties are vital for its handling, storage, and application in precise chemical reactions. The ability to purchase this specific compound is essential for many chemical processes.
The synthesis of beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate involves established organic chemistry procedures. One common method described in literature entails the reaction of a ribose derivative with acetic anhydride and pyridine, followed by extraction and purification. The meticulous control of reaction conditions, such as temperature and reaction time, is critical to achieving high yields and the desired purity level, often exceeding 98% by HPLC. Manufacturers invest significantly in optimizing these synthesis protocols to meet the demanding specifications of the pharmaceutical sector. The price of the raw materials and the complexity of the synthesis contribute to the overall cost of this intermediate.
The primary application of this compound lies in its role as a key intermediate for Clofarabine, an important chemotherapy drug. However, its utility is not limited to this single application. As a protected ribofuranose derivative, it serves as a valuable building block in the synthesis of various nucleoside analogs, which are extensively studied for their potential as antiviral and anticancer agents. Its participation in glycosylation reactions with different nucleobases allows for the creation of diverse molecular structures, essential for drug discovery and development programs. Companies often search for suppliers offering this chemical at a competitive price for their research needs.
In conclusion, beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate is a multifaceted chemical intermediate with a well-defined profile and critical applications. Its synthesis and properties make it indispensable for the production of vital pharmaceuticals and for advancing research in nucleoside chemistry. Reliable sourcing of this compound is a cornerstone for innovation in the life sciences industry.
Perspectives & Insights
Alpha Spark Labs
“Its properties include a melting point in the range of 128-130 °C and limited solubility in common organic solvents like methanol.”
Future Pioneer 88
“3° in pyridine, is a key characteristic that confirms its stereochemical integrity.”
Core Explorer Pro
“These physical and chemical properties are vital for its handling, storage, and application in precise chemical reactions.”