15811-32-2

Basic information

• Product Name: 2-Fluoro-2',3',5'-triacetoxyadenosine
• Synonyms: 2-fluoro-2',3',5'-triacetoxyadenosine;2-FLUORO-2',3',5'-TRI-O-ACETYLADENOSINE;2-Fluoro-2',3',5'-trioxo-acetyl adenosine;[3,4-diacetyloxy-5-(6-amino-2-fluoro-9H-purin-9-yl)-tetrahydrofuran-2-yl]methyl ethanoate;2-FLUORO-2',3',5'-TRI-O-ACETYLADENOSINE(FLUDARABINE INTERMEDIATE);2',3',5'-Tri-O-acetyl-2-fluoroadenosine;2-Fluoro-2',3',5'-Trioxo-Acethyl Adenosine
• CAS NO: 15811-32-2
• Molecular Formula: C₁₆H₁₈FN₅O₇
• Molecular Weight: 411.34
• EINECS: 1592732-453-0
• Mol File: 15811-32-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 194-197°C
• Boiling Point: 635.4 ºC at 760 mmHg
• Flash Point: 338.1 ºC
• Appearance: /
• Density: 1.684 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.30±0.10(Predicted)
• CAS DataBase Reference: 2-Fluoro-2',3',5'-triacetoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-2',3',5'-triacetoxyadenosine(15811-32-2)
• EPA Substance Registry System: 2-Fluoro-2',3',5'-triacetoxyadenosine(15811-32-2)

Safety Data

• Hazardous Substances Data: 15811-32-2(Hazardous Substances Data)

Usage

General Description

2-Fluoro-2',3',5'-triacetoxyadenosine is a chemical compound with the molecular formula C14H15FN2O9. It belongs to the category of nucleoside and nucleotide analogues, which are synthetic structures similar to naturally occurring nucleosides. Adenosine analogues, like 2-Fluoro-2',3',5'-triacetoxyadenosine, are often used in medicinal chemistry for their potential pharmacological activities. They are typically used as antiviral or antineoplastic agents. As is common with many complex compounds, this chemical is highly specific and may require detailed study to identify potential interactions, impacts, and uses in different scientific fields. However, detailed information about this particular chemical is limited. It is advisable to handle and use it in controlled environments under specialized expert guidance.

Synthetic route

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-difluoropurine (15811-33-3) → 2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2)

Conditions	Yield
In 1,2-dimethoxyethane for 0.25h; Ambient temperature;	85%

2-fluoro-6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (1028367-89-6) → 2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; trifluoroacetic acid In ethyl acetate	80.7%

2,6-diamino-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine (52921-40-1) → 2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2)

Conditions	Yield
With tert.-butylnitrite; hydrogen fluoride In pyridine at -30 - -20℃; for 0.166667h;	48%

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-fluoropurine (3633-28-1) → 2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / HF (60percent), tert-butyl nitrite (TBN) / pyridine / 0.02 h / -30 °C 2: 85 percent / 1,2-dimethoxy-ethane / 0.25 h / Ambient temperature View Scheme

2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2) → 2-fluoroadenosine (146-78-1)

Conditions	Yield
With methanol; ammonia	91.6%
With ammonia In ethanol at 20℃; Solvent;

cyclohexane (110-82-7) + 2-fluoro-6-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (15811-32-2) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-cyclohexyl-2-fluoro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1403611-82-4)

Conditions	Yield
With di-tert-butyl peroxide In neat (no solvent) at 140℃; for 24h; Sealed tube; regioselective reaction;	58%

Upstream product

• 15811-33-3 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-difluoropurine 
• 1028367-89-6 2-fluoro-6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 3633-28-1 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-fluoropurine 
• 52921-40-1 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-diaminopurine 

Downstream Products

• 146-78-1 2-fluoroadenosine 
• 1403611-82-4 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-cyclohexyl-2-fluoro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 

Relevant articles and documents

Nucleic acid related compounds. 34. Non-aqueous diazotization with tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides

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Process for the preparation of fludarabine or fludarabine phosphate from guanosine

A process for the production of fludarabine or fludarabine phosphate is provided, wherein the nucleoside guanosine or a suitable derivative is employed as the starting material. The guanosine starting material is subjected to (a) conversion of the 6-keto group into a 6-amino group, (b) conversion of the 2-amino group to a 2-fluoro group, and (c) conversion of the ribofuranosyl moiety to an arabinofuranosyl moiety. Steps (a), (b), and (c) can be performed individually or concomitantly and in any sequence.