2-Fluoro-3'-deoxyadenosine

Base Information

• Chemical Name: 2-Fluoro-3'-deoxyadenosine
• CAS No.: 15386-69-3
• Molecular Formula: C10H12 F N5 O3
• Molecular Weight: 269.235
• DSSTox Substance ID: DTXSID30432315
• Nikkaji Number: J81.856I
• Wikidata: Q82246390
• ChEMBL ID: CHEMBL3110070
• Mol file: 15386-69-3.mol

Synonyms:15386-69-3;2-fluoro-3'-deoxyadenosine;(2R,3R,5S)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol;2-FLUORO-3/'-DEOXYADENOSINE;(2R,3R,5S)-2-(6-AMINO-2-FLUOROPURIN-9-YL)-5-(HYDROXYMETHYL)OXOLAN-3-OL;Adenosine,3'-deoxy-2-fluoro-;2-Fluoro-cordycepin;2-Fluoro-3-deoxyadenosine;3'-desoxy-2-fluoradenosin;3/'-Desoxy-2-fluoradenosin;SCHEMBL3036901;CHEMBL3110070;DTXSID30432315;(2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

Chemical Property of 2-Fluoro-3'-deoxyadenosine

Chemical Property:

• Melting Point: 259-260 °C
• Boiling Point: 696.7±65.0 °C(Predicted)
• PKA: 13.58±0.60(Predicted)
• PSA: 119.31000
• Density: 2.01±0.1 g/cm3(Predicted)
• LogP: -0.23050
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 269.09241742
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

2-FLUORO-3'-DEOXYADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(C1O)N2C=NC3=C(N=C(N=C32)F)N)CO
• Isomeric SMILES: C1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C(N=C(N=C32)F)N)CO

Technology Process of 2-Fluoro-3'-deoxyadenosine

There total 13 articles about 2-Fluoro-3'-deoxyadenosine 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',3'-dehydro-2-fluoroadenosine → (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol (15386-69-3)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; dimethyl sulfoxide; at 4 - 20 ℃; for 17h; Inert atmosphere;

Reference yield: 62.0%

cordycepin (73-03-0) + 2-fluoroadenine (700-49-2) → (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol (15386-69-3)

Guidance literature:

With recombinant E_. coli purine nucleoside phosphorylase; In aq. phosphate buffer; dimethyl sulfoxide; at 40 ℃; for 120h; pH=7; Enzymatic reaction;

DOI:10.1055/s-0036-1590804

Reference yield: 59.0%

(2R,3R,5S)-2-[6-(N-benzoylbenzamido)-2-fluoro-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate (1504571-43-0) → (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol (15386-69-3)

Guidance literature:

With ammonia; In methanol;

DOI:10.1021/jm401530a

upstream raw materials:

9-(3'-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine

3'-deoxycytidine

2,6-diaminopurine

2-fluoroadenine

Refernces

• 1、 -. "NEW 2' AND/OR 5' AMINO-ACID ESTER PHOSPHORAMIDATE 3'-DEOXY ADENOSINE DERIVATIVES AS ANTI-CANCER COMPOUNDS". Page/Page column 59. . Retrieved 2016/06/14.
• 2、 Barai, Vladimir N.,Zinchenko, Anatoli I.,Eroshevskaya, Ludmilla A.,Zhernosek, Elena V.,Balzarini, Jan,De Clercq, Erik,Mikhailopulo, Igor A.. "Chemo-enzymatic synthesis of 3-deoxy-β-D-ribofuranosyl purines and study of their biological properties". . p. 751 - 753. Retrieved 2007/10/03.