15811-32-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoro-2',3',5'-triacetoxyadenosine is used as an antiviral agent for its ability to inhibit viral replication and reduce the severity of viral infections. Its specific mechanism of action may involve targeting viral enzymes or interfering with the viral life cycle, thereby providing a therapeutic option for treating viral diseases.
2-Fluoro-2',3',5'-triacetoxyadenosine is also used as an antineoplastic agent for its potential to inhibit the growth and proliferation of cancer cells. It may achieve this by interfering with cellular processes essential for tumor development, such as DNA replication, cell division, or angiogenesis. This makes it a valuable compound in the development of cancer treatments and therapies.
Used in Research and Development:
In the field of scientific research, 2-Fluoro-2',3',5'-triacetoxyadenosine serves as a valuable tool for studying the mechanisms of action of nucleoside and nucleotide analogues. Its unique structure and properties allow researchers to investigate its interactions with biological systems, enzyme targets, and potential applications in drug discovery. 2-Fluoro-2',3',5'-triacetoxyadenosine can contribute to the advancement of knowledge in medicinal chemistry and the development of novel therapeutic agents.

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

• 52921-40-1 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-diaminopurine 
• 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 

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 academic research and scientific papers

The preparative method for 2-fluoroadenosine synthesis

The preparative method for the synthesis of 2-fluoroadenosine starting from commercially available guanosine was developed. It included the intermediate formation of 2-amino-6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) purine, which was isolated exclu

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.

Process for the production of 2-fluoropurine derivatives

This invention relates to a process for the production of 2-fluoropurine derivatives from 2-aminopurine derivatives, which are reacted in HF/pyridine or HF/pyridine/H2 O in the presence of a nitrite.