2-Fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine

Base Information

• Chemical Name: 2-Fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine
• CAS No.: 15811-32-2
• Molecular Formula: C16H18FN5O7
• Molecular Weight: 411.347
• European Community (EC) Number: 605-130-7
• NSC Number: 108853
• DSSTox Substance ID: DTXSID50935858
• Mol file: 15811-32-2.mol

Synonyms:15811-32-2;NSC108853;2-Fluoro-2',3',5'-Trioxo-Acetyl Adenosine;2-fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine;SCHEMBL12019516;DTXSID50935858;BCP34392;AKOS032947214;NSC-108853;Fludarabine Intermediate;2',3',5'-Tri-O-acetyl-2-fluoroadenosine;2-Fluoro-2 inverted exclamation mark ,3 inverted exclamation mark ,5 inverted exclamation mark -Trioxo-Acethyl Adenosine

Chemical Property of 2-Fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine

Chemical Property:

• Melting Point: 194-197 ºC
• Boiling Point: 635.4 ºC at 760 mmHg
• PKA: 1.30±0.10(Predicted)
• Flash Point: 338.1 ºC
• PSA: 157.75000
• Density: 1.684 g/cm³
• LogP: 0.45270
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 411.11902609
• Heavy Atom Count: 29
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

2?-3?-5?-Tri-O-acetyl-2-fluoroadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=NC3=C(N=C(N=C32)F)N)OC(=O)C)OC(=O)C

Technology Process of 2-Fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine

There total 6 articles about 2-Fluoro-9-(2,3,5-tri-o-acetylpentofuranosyl)-9h-purin-6-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

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)

Guidance literature:

In 1,2-dimethoxyethane; for 0.25h; Ambient temperature;

DOI:10.1139/v81-375

Reference yield: 80.7%

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)

Guidance literature:

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

DOI:10.1134/S1068162009020071

Reference yield: 50.0%

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

Guidance literature:

upstream raw materials:

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

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-difluoropurine

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-fluoropurine

2-fluoro-6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

Downstream raw materials:

2-fluoroadenosine

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-cyclohexyl-2-fluoro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Refernces

• 1、 Berzin,Dorofeeva,Leonov,Miroshnikov. "The preparative method for 2-fluoroadenosine synthesis". experimental part. p. 193 - 196. Retrieved 2010/04/29.
• 2、 -. "Process for the production of 2-fluoropurine derivatives". . . Retrieved 2008/06/13.