5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS No.: 50-91-9
• Molecular Formula: C9H11FN2O5
• Molecular Weight: 246.195
• Hs Code.: 2933.59
• NSC Number: 758230
• Mol file: 50-91-9.mol

Synonyms:5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;Spectrum_001306;Spectrum2_000667;Spectrum3_000950;Spectrum4_001063;Spectrum5_000694;KBioGR_001386;KBioSS_001786;DivK1c_000635;SPECTRUM1503059;SPBio_000733;SCHEMBL4939702;HMS501P17;KBio1_000635;KBio2_001786;KBio2_004354;KBio2_006922;KBio3_002020;NINDS_000635;HMS1922C03;HMS2092H14;Pharmakon1600-01503059;CCG-40019;NSC758230;NSC-758230;IDI1_000635;SBI-0051758.P002;AB00052306_02;SR-05000002046;SR-05000002046-1

Chemical Property of 5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 148 °C(lit.)
• Boiling Point: 150 °C
• PKA: pKa 7.44 (Uncertain)
• PSA: 104.55000
• Density: 1.64 g/cm³
• LogP: -1.68360
• Storage Temp.: 2-8°C
• Water Solubility.: soluble
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 246.06519962
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

99%, ^*data from raw suppliers

Floxuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22-68-36/37/38-40-20/21/22
• Safety Statements: 22-36-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)F)CO)O
• Isomeric SMILES: C1[C@H]([C@H](OC1N2C=C(C(=O)NC2=O)F)CO)O
• Description: Floxuridine is a nucleoside analog that inhibits the enzyme ribonucleotide reductase, which is involved in the synthesis of DNA. Floxuridine has been shown to inhibit the growth of cancer cells and induce apoptosis in vivo. Floxuridine has also been shown to inhibit tumor growth in animal models by inhibiting the production of reactive oxygen species and upregulating tumor suppressor genes, such as p53. This drug also has inhibitory effects on enzymes that are involved in cell proliferation, such as protein kinase C and tyrosine kinases.
• Uses: Floxuridine USP is used in Palliative treatment of gastrointestinal adenocarcinoma with liver metastases. Antiviral; antineoplastic. renal function diagnosis
• Therapeutic Function: Antiviral, Cancer chemotherapy

Technology Process of 5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

There total 58 articles about 5-fluoro-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-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: 98.0%

5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil (1384553-43-8) → 5-Fluoro-2'-deoxyuridine (50-91-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1039/c2cc33155a

Reference yield: 86.2%

3',5'-di-O-(p-chlorobenzoyl)-5-fluoro-2'-deoxy-β-uridine (1582-79-2,110558-30-0) → 5-Fluoro-2'-deoxyuridine (50-91-9)

Guidance literature:

With methanol; ammonia; at 10 - 25 ℃;

Reference yield: 81.0%

5-fluorouracil (51-21-8) + 7-methyl-2′-deoxyguanosine hydroiodide → 5-Fluoro-2'-deoxyuridine (50-91-9)

Guidance literature:

With potassium dihydrogenphosphate; Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase; In aq. buffer; at 20 ℃; for 20h; pH=7.5; Enzymatic reaction;

DOI:10.1002/adsc.201701005

upstream raw materials:

5-fluoro-O^3'_,O5'-bis-(4-methyl-benzoyl)-2'-deoxy-uridine

3',5'-di-O-(p-chlorobenzoyl)-5-fluoro-2'-deoxy-β-uridine

2'-deoxyuridine

acetyl hypofluorite

Downstream raw materials:

5'-O-acetyl-floxuridine

Acetic acid (2R,3S)-2-acetoxymethyl-5-((S)-5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

3′-O-acetyl-5-fluoro-2′-deoxyuridine

1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Onishi,Kawaguchi,Nagai. "In vitro drug release from macromolecule-drug conjugates of 3'-(7-carboxyheptanoyl)-5-fluoro-2'-deoxyuridine with decylenediamine-dextran T70 of poly-L-lysine". . p. 3370 - 3374. Retrieved 1987.
• 2、 Britos, Claudia N.,Cappa, Valeria A.,Rivero, Cintia W.,Sambeth, Jorge E.,Lozano, Mario E.,Trelles, Jorge A.. "Biotransformation of halogenated 2′-deoxyribosides by immobilized lactic acid bacteria". . p. 49 - 53. Retrieved 2012.
• 3、 -. "FLOXURIDINE SYNTHESIS". Page/Page column 33-34. . Retrieved 2019/04/11.