5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidine-2,4-dione
• CAS No.: 145986-11-4
• Molecular Formula: C₈H₉FN₂O₄S
• Molecular Weight: 248.235
• European Community (EC) Number: 875-647-2
• UNII: 7D832RLM83
• DSSTox Substance ID: DTXSID10932106
• Nikkaji Number: J524.974K
• Wikidata: Q82907768
• ChEMBL ID: CHEMBL301450
• Mol file: 145986-11-4.mol

Synonyms:2',3',5-FTU;2',3'-dideoxy-5-fluoro-3'-thiauridine

Chemical Property of 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidine-2,4-dione

Chemical Property:

• Melting Point: 192-194°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 109.62000
• Density: 1.65g/cm³
• LogP: -0.74390
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Heated), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 248.02670611
• Heavy Atom Count: 16
• Complexity: 362

Purity/Quality:

97% ^*data from raw suppliers

cis5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(OC(S1)CO)N2C=C(C(=O)NC2=O)F
• Isomeric SMILES: C1[C@H](O[C@H](S1)CO)N2C=C(C(=O)NC2=O)F
• Uses: Antiviral nucleoside analog, also an impurity found in emtricitabine (E525000).

Technology Process of 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidine-2,4-dione

There total 2 articles about 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidine-2,4-dione 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: 30.4%

(2R,5SR)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>uracil → (-)-(2R,5S)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>uracil (143790-05-0,145986-12-5,145986-11-4,149819-47-6) + (+)-(2R,5R)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>uracil (143790-05-0,145986-12-5,145986-11-4,149819-47-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jm00054a001

Reference yield: 30.4%

(2R,5SR)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>uracil → (-)-(2R,5S)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>uracil (143790-05-0,145986-12-5,145986-11-4,149819-47-6) + (+)-(2R,5R)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>uracil (143790-05-0,145986-12-5,145986-11-4,149819-47-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jm00054a001