5-Fluorouracil arabinoside

Base Information

• Chemical Name: 5-Fluorouracil arabinoside
• CAS No.: 18814-21-6
• Molecular Formula: C₉H₁₁FN₂O₆
• Molecular Weight: 262.195
• NSC Number: 258350,519273,406444,146604
• DSSTox Substance ID: DTXSID40859332
• Mol file: 18814-21-6.mol

Synonyms:5-Fluorouracil arabinoside;18814-21-6;MLS002702026;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-pyrimidine-2,4-dione;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione;NSC146604;5-FLUORO-1-(beta-L-RIBOFURANOSYL)URACIL;FUrd;WLN: T6NVMVJ EF A-ET5OTJ B1Q CQ DQ;MFCD00036832;NSC-146604;AFU;5-fluoro-1-pentofuranosylpyrimidine-2,4(1h,3h)-dione;Neuro_000082;SCHEMBL19901621;SCHEMBL21423048;DTXSID40859332;NSC258350;NSC406444;NSC519273;STK682589;AKOS005597041;AKOS015960593;NSC-258350;NSC-406444;NSC-519273;SB67392;AC-11749;AC-32304;LS-13623;NCI60_000997;PD011722;SMR000565155;SY016933;FT-0600892;FT-0692734;FT-0771689;FT-0774790;AMINO-BENZO[B]THIOPHEN-3-YL-ACETICACID;5-fluoro-4-hydroxy-1-pentofuranosylpyrimidin-2(1H)-one;1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-4-hydroxypyrimidin-2(1H)-one

Chemical Property of 5-Fluorouracil arabinoside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 124.78000
• Density: 1.77g/cm³
• LogP: -2.71280
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 262.06011424
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)F

Technology Process of 5-Fluorouracil arabinoside

There total 14 articles about 5-Fluorouracil arabinoside 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: 96.0%

1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-fluorouracil (77180-90-6) + L-uridine (58-96-8) → 1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil (77210-26-5,131-06-6,316-46-1,3803-28-9,4334-80-9,13040-02-3,18814-21-6,61616-89-5,77210-25-4,77210-27-6,77210-28-7,77210-29-8)

Guidance literature:

In methanol; ammonia;

Reference yield: 95.0%

1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil (446251-78-1) → 1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil (77210-26-5,131-06-6,316-46-1,3803-28-9,4334-80-9,13040-02-3,18814-21-6,61616-89-5,77210-25-4,77210-27-6,77210-28-7,77210-29-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00230-2

Reference yield: 94.0%

C25H21FN2O9 (849342-81-0) → 1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil (77210-26-5,131-06-6,316-46-1,3803-28-9,4334-80-9,13040-02-3,18814-21-6,61616-89-5,77210-25-4,77210-27-6,77210-28-7,77210-29-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1016/j.bmc.2004.12.011

upstream raw materials:

1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-fluorouracil

1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil

C₂₅H₂₁FN₂O₉

1,2-di-O-isopropylidene-3,5-di-O-benzoyl-α-L-ribofuranose

Refernces

• 1、 Shi, Junxing,Du, Jinfa,Ma, Tianwei,Pankiewicz, Krzysztof W.,Patterson, Steven E.,Tharnish, Phillip M.,McBrayer, Tamara R.,Stuyver, Lieven J.,Otto, Michael J.,Chu, Chung K.,Schinazi, Raymond F.,Watanabe, Kyoichi A.. "Synthesis and anti-viral activity of a series of D- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system". . p. 1641 - 1652. Retrieved 2007/10/03.
• 2、 Griffon, Jean-Francois,Mathe, Christophe,Faraj, Abdesslem,Aubertin, Anne-Marie,De Clercq, Erik,Balzarini, Jan,Sommadossi, Jean-Pierre,Gosselin, Gilles. "Stereospecific synthesis and biological evaluations of β-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine". . p. 447 - 460. Retrieved 2007/10/03.