Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside

Base Information

• Chemical Name: Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside
• CAS No.: 109304-16-7
• Molecular Formula: C10H11FN4O3
• Molecular Weight: 254.22
• Mol file: 109304-16-7.mol

Synonyms:Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside;9-(2'-Deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine;9-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purine

Chemical Property of Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside

Chemical Property:

• Melting Point: 173 - 175 °C (methanol)
• PSA: 93.29000
• LogP: -0.58500

Purity/Quality:

97% ^*data from raw suppliers

(2R,3R,4S,5R)-4-Fluoro-2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside

There total 7 articles about Purine -9-beta-D-(2'-deoxy-2'-fluoro) arabinoriboside 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: 53.0%

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine-6-thiol (109304-05-4) → 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine (109304-16-7)

Guidance literature:

nickel; In water; for 2h; Heating;

DOI:10.1248/cpb.37.336

Reference yield:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) → 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine (109304-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) celite / 1.) Hg salt formation; 2.) xylene, reflux

2: thiourea / ethanol / Heating

3: 64.5 percent / NH₃/MeOH / 72 h / 0 °C

4: 53 percent / Raney Ni / H₂O / 2 h / Heating

With methanol; Celite; ammonia; thiourea; nickel; In ethanol; water;

DOI:10.1248/cpb.37.336

Reference yield:

6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (109304-00-9) → 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine (109304-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: thiourea / ethanol / Heating

2: 64.5 percent / NH₃/MeOH / 72 h / 0 °C

3: 53 percent / Raney Ni / H₂O / 2 h / Heating

With methanol; ammonia; thiourea; nickel; In ethanol; water;

DOI:10.1248/cpb.37.336

upstream raw materials:

purine

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)purine-6-thiol

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide

Refernces

• 1、 Chu,Matulic-Adamic,Huang,Chou,Burchenal,Fox,Watanabe. "Nucleosides. CXXXV. Synthesis of some 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purines and their biological activities". . p. 336 - 339. Retrieved 2007/10/02.