1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose

1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose

1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose (CAS No. 10300-21-7) is a synthetic compound that serves as a versatile building block in organic synthesis, particularly in the preparation of nucleoside analogs. It is characterized by its unique molecular structure, which includes multiple functional groups that enhance its reactivity and utility in chemical reactions.

Chemical Properties

• CAS Number: 10300-21-7
• MDL Number: MFCD28978524
• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.34 g/mol
• Boiling Point: 442.0 ± 45.0 °C
• Density: 1.27 ± 0.1 g/cm³
• Appearance: Not specified

Synthesis and Preparation

The synthesis of 1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose typically involves several key steps:

1. Methylation: The hydroxyl group at the 3-position of D-ribofuranose is methylated using methyl iodide in the presence of a base like sodium hydride.
2. Acetylation: The hydroxyl groups at the 1 and 2 positions are acetylated using acetic anhydride and a catalyst such as pyridine.
3. Benzoylation: The hydroxyl group at the 5-position is benzoylated using benzoyl chloride in the presence of a base.

These synthetic routes allow for the creation of this compound, which can act as a precursor to various nucleoside derivatives used in biochemical research and pharmaceutical applications.

Applications

1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose is primarily used in:

• Organic Synthesis: As a building block for more complex organic molecules and nucleoside analogs.
• Biochemical Research: Studied for its potential role in biochemical pathways involving ribose derivatives.
• Medicinal Chemistry: Investigated for antiviral and anticancer therapies due to its structural similarity to natural nucleosides.

Biological Activity

The compound acts as a nucleoside analog, mimicking natural nucleotides and interfering with nucleic acid synthesis, which can inhibit the replication of viruses and the proliferation of cancer cells. Its modifications allow it to target enzymes involved in DNA and RNA synthesis, leading to potential therapeutic applications.

Storage Recommendations

Store 1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose at temperatures between 2–8°C to maintain stability over long periods.

In summary, 1,2-Di-O-acetyl-5-benzoyl-3-O-methyl-D-ribofuranose is a significant compound in organic chemistry with applications in nucleoside synthesis and potential therapeutic uses in medicine due to its biological activity as a nucleoside analog.

Citations:

1. https://www.benchchem.com/product/b600145
2. https://gearsolutions.com/features/bevel-gear-strength-rating-the-appropriate-combination-of-fem-with-rating-standards/
3. https://cdn.standards.iteh.ai/samples/79401/6d7c86b9edfb4369b621511f9f340e2c/ISO-10300-1-2023.pdf
4. https://www.mdpi.com/2076-3417/10/24/8898
5. https://gearsolutions.com/features/service-life-of-cylindrical-and-bevel-gears-under-variable-load-and-stresses/
6. https://digitalscholarship.tsu.edu/cgi/viewcontent.cgi?article=1048&context=facpubs