2'-Fluoro-2'-deoxyadenosine

Base Information

• Chemical Name: 2'-Fluoro-2'-deoxyadenosine
• CAS No.: 64183-27-3
• Molecular Formula: C₁₀H₁₂FN₅O₃
• Molecular Weight: 269.235
• Hs Code.: 2934999090
• European Community (EC) Number: 814-045-6
• DSSTox Substance ID: DTXSID60982712
• Nikkaji Number: J531.970F
• Wikidata: Q76009755
• ChEMBL ID: CHEMBL309579
• Mol file: 64183-27-3.mol

Synonyms:2'-deoxy-2'-fluoroadenosine;2'-fluoro-2'-deoxyadenosine;5'-FDA

Chemical Property of 2'-Fluoro-2'-deoxyadenosine

Chemical Property:

• Boiling Point: 628.6 °C at 760 mmHg
• PKA: 12.60±0.70(Predicted)
• Flash Point: 334 °C
• PSA: 119.31000
• Density: 2.01 g/cm³
• LogP: -0.42160
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: Soluble in water.
• XLogP3: 0
• 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:

98% ^*data from raw suppliers

2''-Fluoro-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)F)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)F)N
• Uses: 2'-Fluoro-2'-deoxyadenosine is a potential prodrug for 2-fluroadenine, involves deoxygenation by reduction of the 2'-thiocar-bonylimidazolide with (Tms)3SiH as hydrogen donor.

Technology Process of 2'-Fluoro-2'-deoxyadenosine

There total 86 articles about 2'-Fluoro-2'-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: 93.0%

2'-Deoxy-2'-fluoro-3',5'-di-O-benzyladenosine (137965-15-2) → 2'-fluorodeoxyadenosine (20187-82-0,20227-41-2,64183-27-3,123334-75-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 2585.7 Torr;

DOI:10.1021/jo00028a030

Reference yield: 82.0%

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + 2'-deoxy-2'-fluorouridine (56287-17-3,69123-94-0,784-71-4) → 2'-fluorodeoxyadenosine (20187-82-0,20227-41-2,64183-27-3,123334-75-8)

Guidance literature:

In water; at 37 ℃; for 408h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;

DOI:10.1021/jm00053a015

Reference yield: 74.0%

6-chloro-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (150863-84-6) → 2'-fluorodeoxyadenosine (20187-82-0,20227-41-2,64183-27-3,123334-75-8)

Guidance literature:

With ammonia; at 40 ℃; bomb;

DOI:10.1080/15257779408013260

upstream raw materials:

2'-Deoxy-2'-fluoro-3',5'-di-O-benzyladenosine

adenine

2'-deoxy-2'-fluorouridine

N-(9-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Downstream raw materials:

2'-deoxy-2'-fluoroadenosine 5'-monophosphate

N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide

C₂₇H₃₄FN₇O₅

Refernces

• 1、 -. "ANTIVIRAL DRUG". Paragraph 0184; 0185; 0188; 0189. . Retrieved 2020/11/03.
• 2、 Qiu, Xiaoxia,Huang, Yiyou,Wu, Deyan,Mao, Fei,Zhu, Jin,Yan, Wenzhong,Luo, Hai-Bin,Li, Jian. "Discovery of novel purine nucleoside derivatives as phosphodiesterase 2 (PDE2) inhibitors: Structure-based virtual screening, optimization and biological evaluation". . p. 119 - 133. Retrieved 2017/11/30.