2'-Deoxy-2,2'-difluoro-adenosine

Base Information

• Chemical Name: 2'-Deoxy-2,2'-difluoro-adenosine
• CAS No.: 147048-53-1
• Molecular Formula: C₁₀H₁₁F₂N₅O₃
• Molecular Weight: 287.226
• Mol file: 147048-53-1.mol

Synonyms:2'-Deoxy-2,2'-difluoro-adenosine

Chemical Property of 2'-Deoxy-2,2'-difluoro-adenosine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

9-(2''-Deoxy-2''-fluoro-b-D-ribofuranosyl)-2-fluoroadenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-Deoxy-2,2'-difluoro-adenosine

There total 21 articles about 2'-Deoxy-2,2'-difluoro-adenosine 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: 77.0%

2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (134444-47-6) → 2'-Deoxy-2,2'-difluoro-adenosine (147048-53-1)

Guidance literature:

With tert.-butylnitrite; pyridine hydrofluoride; In pyridine; at 6 - 12 ℃; for 3h; Cooling with acetone-dry ice; Inert atmosphere;

Reference yield: 64.0%

2'-deoxy-3',5'-di-O-benzoyl-2,2'-difluoroadenosine (156357-17-4) → 2'-Deoxy-2,2'-difluoro-adenosine (147048-53-1)

Guidance literature:

With lithium hydroxide; In water; acetonitrile; for 20h; Ambient temperature;

DOI:10.1080/15257779408013243

Reference yield: 45.0%

2-fluoroadenine (700-49-2) + 2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4) → 2'-Deoxy-2,2'-difluoro-adenosine (147048-53-1)

Guidance literature:

In water; at 37 ℃; for 1224h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;

DOI:10.1021/jm00053a015

upstream raw materials:

2-fluoroadenine

2'-deoxy-2'-fluorouridine

2'-deoxy-3',5'-di-O-benzoyl-2,2'-difluoroadenosine

2-iodo-6-methoxy-9-(β-D-ribofuranosyl)purine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2,2'-difluoro-2'-deoxyadenosine

5'-O-(4,4'-dimethoxytrityl)-3'-O-succinyl-2,2'-difluoro-2'-deoxy adenosine triethylamine

[5'-O-(4,4'-dimethoxytrityl)-2,2'-difluoro-2'-deoxyadenosin-3'-O-yl]-N,N-diisopropylaminocyanoethoxy phosphoramidite

2-methoxy-2'-deoxy-2'-fluoroadenosine

Refernces

• 1、 -. "NON-NATURAL RIBONUCLEOTIDES, AND METHODS OF USE THEREOF". Page/Page column 111. . Retrieved 2009/10/22.
• 2、 Maruyama,Utsumi,Sato,Richman. "Synthesis and anti-HIV activity of 2-substituted 2'-deoxy-2'- fluoroadenosines". . p. 1219 - 1230. Retrieved 2007/10/02.