Adenosine, 2'-deoxy-2-fluoro-

Base Information

• Chemical Name: Adenosine, 2'-deoxy-2-fluoro-
• CAS No.: 21679-12-9
• Molecular Formula: C10H12 F N5 O3
• Molecular Weight: 269.235
• Hs Code.: 2934999090
• NSC Number: 123799,114093
• DSSTox Substance ID: DTXSID30944281
• Mol file: 21679-12-9.mol

Synonyms:Adenosine, 2'-deoxy-2-fluoro-;21679-13-0;9-(2-deoxypentofuranosyl)-2-fluoro-9h-purin-6-amine;CHEMBL279654;SCHEMBL23982169;DTXSID30944281;BDBM50008363;NSC114093;NSC123799;NSC-123799;PD042436;FT-0774800

Chemical Property of Adenosine, 2'-deoxy-2-fluoro-

Chemical Property:

• Appearance/Colour: white to of-white crystals
• Melting Point: 218 °C (dec.)
• Boiling Point: 696.7 °C at 760 mmHg
• Flash Point: 375.1 °C
• PSA: 119.31000
• Density: 2.01 g/cm³
• LogP: -0.23050
• XLogP3: 0.3
• 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%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=C(N=C32)F)N)CO)O
• Uses: 2-Fluoro-2’-deoxyadenosine is an analog tested to the susceptibility of clinical metronidazole-resistant Trichomonas vaginalis. Also, it is one of two purine nucleoside that forms a suicide system as a powerful killing and bystander effects on tumor cells.

Technology Process of Adenosine, 2'-deoxy-2-fluoro-

There total 18 articles about Adenosine, 2'-deoxy-2-fluoro- 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: 98.0%

2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine (259528-01-3) → 2-fluoro-2'-deoxyadenosine (21679-12-9)

Guidance literature:

With tetraethylammonium fluoride; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1080/15257770008035007

Reference yield: 87.0%

2-fluoro-9-(3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-D-erythro-pentofuranosyl)adenine (675598-20-6) → 2-fluoro-2'-deoxyadenosine (21679-12-9)

Guidance literature:

With tetraethylammonium fluoride; In acetone; at 20 ℃;

DOI:10.1081/NCN-120025237

Reference yield: 74.0%

2'-deoxyuridine (951-78-0,63844-76-8) + 2-fluoroadenine (700-49-2) → 2-fluoro-2'-deoxyadenosine (21679-12-9)

Guidance literature:

With aeromonas hydrophila CECT 4226; at 45 ℃; for 1h; pH=7; aq. phosphate buffer; Enzymatic reaction;

DOI:10.3109/10242422.2010.538949

upstream raw materials:

2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine

2-fluoro-9-(3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-D-erythro-pentofuranosyl)adenine

D-2-deoxyribose

2-fluoroadenine

Downstream raw materials:

2-fluoroadenine

8-phenyl-2-(N-piperidyl)-2'-deoxyadenosine

2-deoxy–α-D-ribose 1-phosphate

Refernces

• 1、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.
• 2、 Zhou, Xinrui,Szeker, Kathleen,Jiao, Lin-Yu,Oestreich, Martin,Mikhailopulo, Igor A.,Neubauer, Peter. "Synthesis of 2,6-dihalogenated purine nucleosides by thermostable nucleoside phosphorylases". . p. 1237 - 1244. Retrieved 2015/04/22.