3'-Fluorothymidine

Base Information

• Chemical Name: 3'-Fluorothymidine
• CAS No.: 25526-93-6
• Molecular Formula: C10H13FN2O4
• Molecular Weight: 244.223
• Hs Code.: 29349990
• NSC Number: 140025
• DSSTox Substance ID: DTXSID20860345
• Mol file: 25526-93-6.mol

Synonyms:(18)FLT cpd;(18F)3'-deoxy-3'-fluorothymidine;(18F)FLT;1-(3'-fluoro-3'-deoxy-beta-D-erythropentofuranosyl)thymine;18F-FLT;3'-(F-18)fluoro-3'-deoxythymidine;3'-deoxy-3'-(18F)fluorothymidine;3'-deoxy-3'-fluorothymidine;3'-fluoro-2',3'-dideoxythymidine;3'-fluoro-3'-deoxythymidine;3'-fluorothymidine;alovudine;FDDT

Chemical Property of 3'-Fluorothymidine

Chemical Property:

• Appearance/Colour: Colourless solid
• Melting Point: 176-178 °C(lit.)
• PKA: 9.55±0.10(Predicted)
• PSA: 84.32000
• Density: 1.44 g/cm³
• LogP: -0.53710
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 244.08593506
• Heavy Atom Count: 17
• Complexity: 385

Purity/Quality:

99.0%min ^*data from raw suppliers

Vascular Endothelial Growth Factor Receptor 1 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)F
• Uses: An antiviral agent Promising antiviral agent possessing activity similar to other 3′-deoxy-3′-substituted thymidines.

Technology Process of 3'-Fluorothymidine

There total 71 articles about 3'-Fluorothymidine 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: 97.0%

5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine (290371-78-7) → alovudine (25526-93-6)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 45 ℃; for 0.166667h;

DOI:10.1021/jm201482p

Reference yield: 93.0%

1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone (145688-92-2) → alovudine (25526-93-6)

Guidance literature:

With Dowex 50; In ethanol; water;

DOI:10.1016/S0040-4039(00)73186-8

Reference yield: 90.0%

1-(2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)thymine (585540-19-8) → alovudine (25526-93-6)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In 1,4-dioxane; for 2h; Heating;

DOI:10.1021/jo0340859

upstream raw materials:

5'-O-trityl-2,3'-anhydrothymidine

2,3'-anhydrothymidine

1-<2,3-Dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-α/β-D-erythro-pentofuranosy>-5-methyl-2,4(1H,3H)-pyrimidinedione

2,2-Dimethyl-propionic acid (2R,3S)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Downstream raw materials:

3'-fluoro-5'-O-tert-butyldiphenylsilyl-3'-deoxythymidine

5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

5-(2,2,2-trifluoroethoxy)methyl-3'-fluoro-5'-O-tert-butyldiphenylsilyl-2',3'-dideoxyuridine

5-[bis(2,2,2-trifluoroethoxy)methyl]-3'-fluoro-5'-O-tert-butyldiphenylsilyl-2',3'-dideoxyuridine

Refernces

• 1、 Agarwal, Hitesh Kumar,Parang, Keykavous. "Application of solid-phase chemistry for the synthesis of 3′-fluoro-3′-deoxythymidine". . p. 317 - 322. Retrieved 2007.
• 2、 -. "Radiologic Agents for Monitoring Alzheimer's Disease Progression and Evaluating a Response to Therapy and Processes for the Preparation of Such Agents". Page/Page column 6. . Retrieved 2009/05/28.