5-Ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-Ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione
• CAS No.: 15176-29-1
• Molecular Formula: C11H16 N2 O5
• Molecular Weight: 256.258
• Hs Code.: 29349990
• NSC Number: 758405
• Wikidata: Q27189576
• ChEMBL ID: CHEMBL2138464
• Mol file: 15176-29-1.mol

Synonyms:5-ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione;5-ethyl-1-[4-hydroxy-3-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;KBio2_005485;Spectrum_000009;Spectrum2_001960;Spectrum3_001569;Spectrum4_000869;Spectrum5_001002;BSPBio_003078;KBioGR_001537;KBioSS_000349;DivK1c_000465;SPECTRUM1503214;SPBio_002059;CHEMBL2138464;HMS501H07;KBio1_000465;KBio2_000349;KBio2_002917;KBio3_002578;CHEBI:110195;NINDS_000465;HMS1922I15;HMS2092N18;Pharmakon1600-01503214;NSC758405;AKOS030241111;CCG-213128;IDI1_000465;NCGC00095019-02;NCGC00095019-03;NCGC00178311-01;SBI-0051787.P002;AB00052327_02;SR-05000001551;SR-05000001551-1;BRD-A62505706-001-03-1;Q27189576

Chemical Property of 5-Ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione

Chemical Property:

• Melting Point: 152-153°
• Boiling Point: °Cat760mmHg
• PKA: 9.98(at 25℃)
• Flash Point: °C
• PSA: 104.55000
• Density: 1.389 g/cm³
• LogP: -1.26030
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 256.10592162
• Heavy Atom Count: 18
• Complexity: 395

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Ethyl-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CN(C(=O)NC1=O)C2C(C(CO2)O)CO
• Uses: antiallergic, mast cell degranulation inhibitor, angiogenesis blocker Edoxudine was found to be a modulator of both antitumor action and pharmacokinetics of 5-Fluorouracil (F596000), a potent antineoplastic agent in clinical use. 5-Ethyl-2’-deoxyuridine was found to be a modulator of both antitumor action and pharmacokinetics of 5-Fluorouracil (F596000), a potent antineoplastic agent in clinical use.

Technology Process of 5-Ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione

There total 22 articles about 5-Ethyl-1-[4-hydroxy-3-(hydroxymethyl)-2-oxolanyl]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: 97.0%

2'-deoxy-5-ethynyluridine (61135-33-9) → edoxudine (15176-29-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h; under 760 Torr;

DOI:10.1021/jo00159a012

Reference yield: 81.0%

5-ethyluracil (4212-49-1) + 7-methyl-2′-deoxyguanosine hydroiodide → edoxudine (15176-29-1)

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

Reference yield: 68.0%

5-ethyluracil (4212-49-1) + 2'-deoxyuridine (951-78-0,63844-76-8) → edoxudine (15176-29-1)

Guidance literature:

at 37 ℃; for 18h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E_. coli, ammonium acetate buffer pH 5.8;

DOI:10.1135/cccc19942303

upstream raw materials:

5-(1-methoxy-2-iodoethyl)-2'-deoxyuridine

5-vinyl-2'-deoxyuridine

2'-deoxy-5-ethynyluridine

5-ethyluracil

Downstream raw materials:

3'-O-Acetyl-5-ethyl-2'-deoxyuridine

5'-O-Trityl-5-ethyl-2'-deoxyuridine

2'-deoxy-5-ethyl-5'-O-(p-toluenesulphonyl)uridine

1-(2,3-dideoxy-3-fluoro-5-O-trityl-β-D-erythro-pentofuranosyl)-5-ethyluracil

Refernces

• 1、 Takenaka, Keiko,Muraoka, Masako,Tsuji, Tadakazu. "Synthesis of 5-ethylpyrimidine nucleoside analogs". . p. 669 - 673. Retrieved 1997.
• 2、 Drenichev, Mikhail S.,Alexeev, Cyril S.,Kurochkin, Nikolay N.,Mikhailov, Sergey N.. "Use of Nucleoside Phosphorylases for the Preparation of Purine and Pyrimidine 2′-Deoxynucleosides". . p. 305 - 312. Retrieved 2018.
• 3、 Hatano, Akihiko,Kurosu, Masayuki,Yonaha, Susumu,Okada, Munehiro,Uehara, Sanae. "One-pot approach to functional nucleosides possessing a fluorescent group using nucleobase-exchange reaction by thymidine phosphorylase". . p. 6900 - 6905. Retrieved 2013/10/08.