Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine (CAS: 161599-46-8), also known as 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine, is an organic nucleoside derivative with fluorine and acetyl functional groups. It appears as a white to almost white crystalline powder or crystal, odorless, and chemically stable under proper storage conditions. As a critical pharmaceutical intermediate, it is mainly used for the synthesis of capecitabine, an oral nucleoside antitumor drug clinically applied in the treatment of metastatic colorectal cancer, breast cancer, colon cancer, and gastric cancer. It also serves as a research reagent in organic synthesis and pharmaceutical quality control.
Uses
Pharmaceutical Intermediates: The most important application is as a key intermediate for synthesizing capecitabine, a widely used oral antitumor drug with a broad anticancer spectrum and few side effects. It can also be used as a reference material for impurity detection in related pharmaceutical quality control processes.
Laboratory & Industrial Applications: Used as a reagent in organic synthesis, especially in the preparation of fluorinated nucleoside derivatives. In laboratory settings, it serves as a reference standard for analytical testing such as high-performance liquid chromatography (HPLC). Industrially, it is produced on a large scale for pharmaceutical manufacturing, with optimized synthesis methods enabling high purity and yield.
Molecular Formula & Structure
- Molecular Formula: C??H??FN?O?
- Molecular Weight: 329.28 g/mol
- IUPAC Name: 5'-Deoxy-5-fluoro-2',3'-di-O-acetylcytidine
- Synonyms: 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine;
- EINECS Number: 605-260-4
- CAS Number: 161599-46-8
- SMILES Code: C(C@H)1O(C@@H)(N2C=C(F)C(N)=NC2=O)(C@H)(OC(=O)C)(C@@H)1OC(=O)C
- Chemical Structure: A nucleoside derivative with a cytidine core, featuring two acetyl groups (-OCOCH?) at the 2' and 3' positions, a fluorine atom (-F) at the 5 position, and a deoxy group (missing hydroxyl) at the 5' position. This structure is crucial for its role as an intermediate in antitumor drug synthesis.
Physical & Chemical Properties
- Appearance: White to almost white crystalline powder or crystal, odorless.
- Density: 1.57 ± 0.1 g/cm3 (predicted); Melting Point: 196–198 °C (lit.).
- Solubility: Soluble in methanol; solubility in other organic solvents and water is not explicitly reported.
- Boiling Point: 427.4 ± 55.0 °C (predicted); Flash Point: 212.3 °C.
- Stability: Stable under normal temperature and dry conditions; incompatible with strong oxidants and strong bases; avoid exposure to heat, moisture, and direct sunlight.
- Toxicity: Specific acute toxicity data is not available; as a pharmaceutical intermediate, it should be handled with proper protective measures to avoid skin, eye, and respiratory contact[3]. Safety specification: 24/25 (avoid contact with skin and eyes).
- pKa: 2.49 ± 0.10 (predicted); LogP: Not available; PSA: Not available.
Synthesis & Storage
- Synthesis: Industrially prepared via multiple methods, including glycosylation reaction of 1,2,3-tri-O-acetyl-5-deoxyribose with bis-silylated 5-fluorocytosine catalyzed by polymer-supported Lewis acid, which offers high yield (up to 76.6%) and purity (up to 99.6%), suitable for industrial production[1]. It can also be prepared by acetylation of 5'-deoxy-5-fluorocytidine with acetic anhydride, or via nucleophilic reaction and condensation reaction involving 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose.
- Storage: Sealed in airtight, light-proof containers; stored in a cool, dark place at 2–8 °C; keep dry; avoid moisture, heat, and direct sunlight; shelf life is 2 years under proper storage conditions.
- Safety: Operate in a well-ventilated fume hood; wear professional protective gear (nitrile gloves, goggles, lab coat); avoid breathing dust or vapors; wash skin and eyes thoroughly after contact; avoid eating, drinking, or smoking during handling; keep out of reach of children.
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