2-AMino-6-chloropurine -9-beta-D-(2'-deoxy-2'-fluoro)-arabinoriboside

Base Information

• Chemical Name: 2-AMino-6-chloropurine -9-beta-D-(2'-deoxy-2'-fluoro)-arabinoriboside
• CAS No.: 144924-88-9
• Molecular Formula: C10H11ClFN5O3
• Molecular Weight: 303.68
• Mol file: 144924-88-9.mol

Synonyms:2-AMino-6-chloropurine -9-beta-D-(2'-deoxy-2'-fluoro)-arabinoriboside;2-AMino-6-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine;6-Chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purin-2-amine

Chemical Property of 2-AMino-6-chloropurine -9-beta-D-(2'-deoxy-2'-fluoro)-arabinoriboside

Chemical Property:

• PSA: 119.31000
• LogP: 0.23180

Purity/Quality:

97% ^*data from raw suppliers

(2R,3R,4S,5R)-5-(2-Amino-6-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-AMino-6-chloropurine -9-beta-D-(2'-deoxy-2'-fluoro)-arabinoriboside

There total 7 articles about 2-AMino-6-chloropurine -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: 75.0%

2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine (118373-61-8) → 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranos-1'-yl)-2-amino-6-chloropurine (144924-88-9)

Guidance literature:

With ammonia; In methanol; for 4h;

DOI:10.1080/15257779408013236

Reference yield:

2-Amino-6-chloropurin (10310-21-1) + 2-deoxy-2-fluoro-α-D-arabinofuranose 1-phosphate (850883-62-4) → 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranos-1'-yl)-2-amino-6-chloropurine (144924-88-9)

Guidance literature:

purine nucleoside phosphorylase; In water; at 50 ℃; for 336h; pH=7.5; Aqueous phosphate buffer; Enzymatic reaction;

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 9-(2'-deoxy-2'-fluoro-β-D-arabinofuranos-1'-yl)-2-amino-6-chloropurine (144924-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

2: 1.) bis(trimethylsilyl)acetamide, 2.) Hg(CN)2 / 1.) CH₃CN, room temperature, 30 min, 2.) C₆H₆, reflux, 3 h

3: 75 percent / NH₃ / methanol / 4 h

With ammonia; hydrogen bromide; mercury(II) cyanide; acetic acid; bis-(trimethylsilyl)acetamide; In methanol; dichloromethane;

DOI:10.1080/15257779408013236

upstream raw materials:

2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

2-Amino-6-chloropurin

Downstream raw materials:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Refernces

• 1、 Sivets, Grigorii G.. "Syntheses of 2′-deoxy-2′-fluoro-β-d-arabinofuranosyl purine nucleosides via selective glycosylation reactions of potassium salts of purine derivatives with the glycosyl bromide". supporting information. p. 268 - 271. Retrieved 2016/01/12.
• 2、 -. "ALPHA-1-PHOSPHORYLATED-2-DEOXY-2-FLUOROARABINOSIDE AND PROCESS FOR PRODUCING 2 -DEOXY-2 -FLUORO-BETA-D-ARABINONUCLEOSID E". Page/Page column 19. . Retrieved 2008/06/13.