Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)-

Base Information

• Chemical Name: Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)-
• CAS No.: 55774-30-6
• Molecular Formula: C8H9 F N2 O3
• Molecular Weight: 200.169
• UNII: 4D5LOR404U
• Nikkaji Number: J96.663K
• Wikidata: Q27259434
• ChEMBL ID: CHEMBL3272485
• Mol file: 55774-30-6.mol

Synonyms:55774-30-6;Tegafur, (S)-;Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)-;5-fluoro-1-[(2S)-oxolan-2-yl]pyrimidine-2,4-dione;4D5LOR404U;S-Ftorafur;(S)-5-Fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;UNII-4D5LOR404U;(S)-1-(TETRAHYDROFURAN-2-YL)-5-FLUOROURACIL;S-1-(Tetrahydrofuran-2-yl)-5-fluorouracil;(S)-tegafur;2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (S)-;SCHEMBL7698456;CHEMBL3272485;5-fluoro-1-[(2S)-oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione;EN300-8671643;Q27259434;5-fluoro-1-[(2S)-tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione;2,4(1H,3H)-PYRIMIDINEDIONE, 5-FLUORO-1-((2S)-TETRAHYDRO-2-FURANYL)-

Chemical Property of Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)-

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 64.09000
• Density: 1.45g/cm³
• LogP: -0.01530
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 200.05972032
• Heavy Atom Count: 14
• Complexity: 316

Purity/Quality:

97% ^*data from raw suppliers

(S)-1-(TETRAHYDROFURAN-2-YL)-5-FLUOROURACIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)N2C=C(C(=O)NC2=O)F
• Isomeric SMILES: C1C[C@H](OC1)N2C=C(C(=O)NC2=O)F

Technology Process of Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)-

There total 2 articles about Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (S)- 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:

(S)-1-(2,5-dihydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione → (S)-5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (55774-30-6,65732-47-0,79107-97-4) + 5-fluoro-1-((R)-tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione (37076-68-9,65732-47-0,79107-97-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 0.166667h; under 760.051 Torr; Overall yield = 78 %; Overall yield = 16.0 mg;

DOI:10.1021/acs.orglett.7b02332

Reference yield:

(S,E)-5-fluoro-1-(1-(hex-2-enyloxy)allyl)pyrimidine-2,4(1H,3H)-dione → (S)-5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (55774-30-6,65732-47-0,79107-97-4) + 5-fluoro-1-((R)-tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione (37076-68-9,65732-47-0,79107-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 0.17 h / 40 °C

2: palladium on activated charcoal; hydrogen / methanol / 0.17 h / 20 °C / 760.05 Torr

With Hoveyda-Grubbs catalyst second generation; palladium on activated charcoal; hydrogen; In methanol; dichloromethane;

DOI:10.1021/acs.orglett.7b02332

Reference yield:

(S)-5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (55774-30-6,65732-47-0,79107-97-4) → 5-fluorouracil (51-21-8)

Guidance literature:

With glucose-6-phosphate dehydrogenase; glucose-6-phosphate; CYP₂A_6.1, wild-type; NADP; magnesium chloride; In aq. buffer; at 37 ℃; pH=7.4; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1124/dmd.114.058008

Downstream raw materials:

5-fluorouracil

Refernces