1-[(2S,3S,4R,5S)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-YL]-5-fluoropyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[(2S,3S,4R,5S)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-YL]-5-fluoropyrimidine-2,4(1H,3H)-dione
• CAS No.: 3094-09-5
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.195
• Hs Code.: 2933.59
• European Community (EC) Number: 221-440-1
• Wikipedia: Doxifluridine
• Mol file: 3094-09-5.mol

Synonyms:3094-09-5;1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione;1-[(2S,3S,4R,5S)-3,4-DIHYDROXY-5-METHYLTETRAHYDROFURAN-2-YL]-5-FLUOROPYRIMIDINE-2,4(1H,3H)-DIONE;MFCD00866530;5'-desoxy-5-fluorouridin;NCGC00093926-04

Chemical Property of 1-[(2S,3S,4R,5S)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-YL]-5-fluoropyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 188-192 °C(lit.)
• Refractive Index: 20 ° (C=1, H2O)
• PKA: 7.4(at 25℃)
• PSA: 104.55000
• Density: 1.63 g/cm³
• LogP: -1.68520
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 246.06519962
• Heavy Atom Count: 17
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

Doxifluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@H]([C@@H](O1)N2C=C(C(=O)NC2=O)F)O)O
• Description: Doxifluridine is a prodrug derivative of 5-fluorouracil (5-FU). As an antineoplastic it is more potent than 5-FU in the treatment of breast, stomach, colon and rectal cancers.
• Uses: A prodrug of 5-Flurouridine. A fluorinated pyrimidine nucleoside with cytostatic activity An antitumor agent efficient in tumors, cell lines or in fibroblasts tranformed by H-ras or trk oncogenes. A metabolite of Capecitabine 5’-Deoxy-5-fluorouridine is a metabolite of the chemotherapeutic agent Capecitabine (C175650). 5’-Deoxy-5-fluorouridine is an antitumor agent efficient in tumors, cell lines or in fibroblasts tranformed by H-ras or trk oncogenes. antineoplastic, pyrimidine antimetabolite

Technology Process of 1-[(2S,3S,4R,5S)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-YL]-5-fluoropyrimidine-2,4(1H,3H)-dione

There total 32 articles about 1-[(2S,3S,4R,5S)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-YL]-5-fluoropyrimidine-2,4(1H,3H)-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: 97.0%

1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil (76462-82-3) → doxifluridine (69260-71-5,71609-07-9,71609-60-4,76462-79-8,106775-49-9,106775-50-2,106775-51-3,3094-09-5)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1002/hlca.19820650525

Reference yield: 95.0%

2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine (77180-87-1) → doxifluridine (69260-71-5,71609-07-9,71609-60-4,76462-79-8,106775-49-9,106775-50-2,106775-51-3,3094-09-5)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 38.0%

5-fluorouracil (51-21-8) + 5'-deoxyuridine (15958-99-3) → doxifluridine (69260-71-5,71609-07-9,71609-60-4,76462-79-8,106775-49-9,106775-50-2,106775-51-3,3094-09-5)

Guidance literature:

With immobilized uridine phosphorylase (E_.C_.2.4.2.1) from Bacillus subtilis; at 25 ℃; for 24h; pH=7.5; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/ejoc.200801096

upstream raw materials:

5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine

2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil

acetyl hypofluorite

Downstream raw materials:

5-fluorouracil

2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

5′-deoxy-2′,3′-O-isopropylidene-5-fluorouridine

1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil

Refernces

Synthesis of 3′(2′)-O-lysophosphatidylnucleosides - A further application of a chemoenzymatic strategy

10.1002/1099-0690(200211)2002:21<3622::AID-EJOC3622>3.0.CO;2-4

The study focuses on the synthesis of 3′(2′)-O-lysophosphatidylnucleosides using a chemoenzymatic approach. The researchers aimed to enhance the cellular uptake of nucleosides by attaching lipophilic moieties, specifically lysophosphatidyl groups, to them. The process involved preparing mono[(2R)-2,3-dihydroxypropyl] esters of 3′-nucleotides from protected nucleoside phosphoramidites and [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol. These esters were then acylated at the C-1 hydroxyl of the glycerol moiety by a lipase-catalyzed transacylation with activated palmitic acid ester in organic solvent, resulting in the formation of 3′-O-lysophosphatidyl-2′-deoxynucleosides. The study also adapted this method to synthesize lysophosphatidyl derivatives of compounds like 5′-deoxy-5-fluorouridine (DFUR) and 5′-deoxy-5′-(methylthio)adenosine (MTA), which lack a 5′-hydroxyl group necessary for the initial 5′-O-lysophosphatidyl conjugation. The synthesized compounds were characterized using spectroscopic techniques, and their interactions with lipid monolayers were tested to demonstrate their enhanced ability to penetrate cell membranes compared to free nucleosides.

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