Brief Description: Beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate is a protected ribose derivative featuring an acetyl group at the anomeric position and benzoyl protections at the 2, 3, and 5 hydroxyl positions. This structure serves as a key synthetic intermediate in nucleoside chemistry, particularly for the preparation of beta-D-ribonucleosides and modified RNA building blocks. Its primary application lies in the pharmaceutical and biochemical fields, where it is utilized as a glycosyl donor in the synthesis of antiviral and anticancer nucleoside analogs. It is also employed in nucleotide prodrugs and for oligonucleotide synthesis. Additionally, it is a valuable tool for constructing labeled or modified nucleosides used in mechanistic studies of nucleic acid metabolism and enzyme inhibition. Product main Properties: 1) Appearance: White to Yellowish Crystal powder 2) Purity: 98% above 3) Melting Point: 128-130 °C 4) Boiling Point:6 21 °C at 760 mmHg 5) Flash Point: 264.3 °C 6) Density: 1.35 g/cm3 7) Refractive Index: 1.61 8) Product manager Email: Joy@coreychem.com Frequently Asked Questions (FAQ): 1）Are there any limitations or special handling precautions associated with this compound? Moisture sensitivity: As a glycosyl donor, it should be stored and handled under anhydrous conditions (desiccator, argon atmosphere) because even trace moisture can hydrolyze the anomeric acetate. Acid sensitivity: The benzoate esters are stable to mild acid but prolonged exposure to strong acids can cause deprotection or acyl migration. Base sensitivity: While the acetate and benzoates resist mild bases, strong nucleophilic bases (e.g., DBU, NaOH) will rapidly cleave the esters, so deprotection must be carefully controlled. Toxicity: Like most benzoylated sugars, it may be irritating to eyes and skin; use standard laboratory PPE (gloves, goggles) and work in a fume hood when heating or handling large quantities.
2)Is this compound stable under normal laboratory conditions? β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate is a stable, crystalline white solid with a melting point of 128–130°C. It should be stored at room temperature in a cool, dark place (below 15°C is recommended), or refrigerated at 2–8°C for long-term storage. It is sensitive to moisture, so keep containers tightly sealed.
3)Can I use this compound for both purine and pyrimidine nucleoside synthesis?
Absolutely. The Vorbrüggen glycosylation is highly versatile and works effectively with a wide range of silylated purine and pyrimidine bases, including adenine, guanine, cytosine, uracil, thymine, and numerous modified heterocycles.
4)How does this product compare to other glycosyl donors? Compared to glycosyl halides (which are often unstable and moisture-sensitive) or thioglycosides (which require different activation conditions), this acetate donor offers an excellent balance of stability, reactivity, and stereoselectivity. The benzoyl protecting group is particularly advantageous because it is removed under mild basic conditions after the glycosylation step, without affecting the newly formed N-glycosidic bond.
Application Cases: 1.Core Role as a Glycosyl Donor in Nucleoside Synthesis This compound is a fully protected ribofuranose derivative featuring an acetyl group at the anomeric (C-1) position and benzoyl protections at the 2-, 3-, and 5-hydroxyl positions. Its primary application is as a glycosyl donor in the synthesis of nucleosides, nucleotides, and their analogs. The anomeric acetate acts as an excellent leaving group under mild Lewis acid catalysis (e.g., TMSOTf, SnCl₄, BF₃·Et₂O). The neighboring 2-O-benzoate group participates in the reaction via an acyloxonium ion, directing incoming nucleobases to attack from the β-face, resulting in high β-stereoselectivity for the formation of naturally occurring β-nucleosides. 2. Applications in Antiviral and Anticancer Drug Synthesis Antiviral Drugs: This protected ribose serves as a key intermediate in the synthesis of antiviral agents, including analogs of Remdesivir, Sofosbuvir, and Ribavirin. Anticancer Agents: It is extensively used as a building block for anticancer nucleoside analogs, such as Gemcitabine analogs and Cladribine. More specifically, it serves as a critical intermediate in the manufacturing of Clofarabine, a purine nucleoside antimetabolite used to treat acute lymphoblastic leukemia (ALL) in children and young adults aged 1 to 21 years. Antibiotics and Other Bioactive Molecules: This compound is also employed in the synthesis of antibiotics such as Puromycin and Cordycepin analogs, as well as modified nucleosides for mRNA vaccine components (e.g., N1-methylpseudouridine pathways) and fluorescent nucleotides for probes and diagnostics. 3.Synthesis of Modified Nucleosides and Building Blocks 7-Deazapurine glycosylation: The compound can be used in the glycosylation of 7-deazapurines, where the glycosylation yield and position depend strongly on 7-substituents (H vs. halogen) and amino protecting groups. It has been used to synthesize compounds like 5-Bromo-4-chloro-2-[(N2-isobutyryl){2,3,5-tri-O-benzoyl-β-D-ribofuranosyl}]amino-7H-pyrrolo[2,3-d]pyrimidine. Precursor for phosphoramidites: It serves as a vital precursor for protected ribonucleoside phosphoramidite building blocks used in automated RNA synthesis. After glycosylation, the 5'-OH benzoate is selectively removed and the free hydroxyl is phosphitylated to form the phosphoramidite monomer. 4. Applications in Modified Sugars and Probes The protected ribose scaffold can be further chemically modified before or after glycosylation, such as fluorination, methylation, or other substitutions at specific carbon positions, to create sugar-modified nucleoside analogs used in drug discovery. It is also a valuable tool for constructing labeled or modified nucleosides used in mechanistic studies of nucleic acid metabolism and enzyme inhibition. 5.Other Uses and Applications Inhibitor of neutrophil-keyhole limpet hemocyanin adhesion – the compound has been reported to act as an inhibitor in this biological assay. Azacitidine USP Related Compound B – it is referenced as a standard related compound for azacitidine quality control. Reference standard – often used as a HPLC reference standard (≥98% purity) in pharmaceutical analysis. Locked Nucleic Acids (LNAs) – used as a starting point for LNA modification.
Beyond Nucleosides: A Versatile Building Block While nucleoside synthesis is its primary application, this compound has found use in other areas of synthetic chemistry. It serves as a key intermediate in the preparation of C-nucleosides, nucleoside antibiotics, and carbohydrate-based enzyme inhibitors. Its ability to undergo stereoselective glycosylation makes it invaluable for constructing complex natural products and pharmaceutical candidates containing ribose moieties. For more product info and questions, please contact product manager: Joy@coreychem.com
