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Other Specialized Reagents

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

Category:

Other Specialized Reagents

CAS NO:

97614-43-2

Standard:

BP,USP,

Price Range:

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Main Sales Markets:

North America,Western Europe,Eastern Europe

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Shanghai Sunwise Chemical Co., Ltd.

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Basic Info

CAS Number

97614-43-2

Pharmacopoeia

BP,USP

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Product Description

Pharmaceutical Raw Materials and Intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose is a specialized fluorinated carbohydrate derivative widely utilized in medicinal chemistry and nucleoside research. Its chemical formula is C24H25FO9, and it is identified by the CAS number 101836-78-4. This compound serves as a critical intermediate in the synthesis of modified nucleosides, particularly those designed for antiviral and anticancer therapies. The molecule features a ribofuranose ring where the hydroxyl group at the 2-position has been replaced by a fluorine atom, while the positions at 1, 3, and 5 are protected with benzoyl groups. These benzoyl protecting groups are essential during synthetic sequences to prevent unwanted side reactions at the hydroxyl sites, allowing for precise functionalization elsewhere on the sugar scaffold. The introduction of the fluorine atom at the C2 position significantly alters the metabolic stability and electronic properties of the resulting nucleoside analogs. Fluorine substitution often enhances resistance against enzymatic degradation by cellular phosphatases and nucleosidases, thereby prolonging the biological half-life of the drug candidate. Consequently, this specific building block is frequently employed in the development of potent inhibitors targeting viral polymerases or reverse transcriptases. It plays a pivotal role in constructing analogs such as remdesivir precursors or other nucleotide mimics used to combat RNA viruses like SARS-CoV-2, HIV, and Hepatitis C. Furthermore, its structural rigidity and lipophilicity, derived from the benzoyl esters, facilitate membrane permeability studies and optimize pharmacokinetic profiles in preclinical models. In laboratory settings, researchers utilize 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose under controlled conditions to synthesize complex oligonucleotides and radiolabeled probes for diagnostic imaging. The versatility of this reagent makes it indispensable for high-throughput screening campaigns aimed at discovering novel therapeutics. By enabling the creation of stable, bioactive nucleoside frameworks, this compound bridges the gap between fundamental carbohydrate chemistry and advanced pharmaceutical applications. Its availability supports global efforts in combating infectious diseases and developing targeted cancer treatments through rational drug design. Ultimately, this fluorinated sugar derivative remains a cornerstone reagent in modern organic synthesis, driving innovation in the field of nucleoside-based medicines.