S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate

Base Information

• Chemical Name: S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate
• CAS No.: 647852-33-3
• Molecular Formula: C20H20N2O6S
• Molecular Weight: 416.455
• DSSTox Substance ID: DTXSID10461805
• Wikidata: Q82286222
• Mol file: 647852-33-3.mol

Synonyms:647852-33-3;CTK2A3154;S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate;DTXSID10461805

Chemical Property of S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 416.10420754
• Heavy Atom Count: 29
• Complexity: 749

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C#CCCSC(=O)C3=CC=CC=C3)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C#CCCSC(=O)C3=CC=CC=C3)CO)O

Technology Process of S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate

There total 6 articles about S-[4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-3-ynyl] benzenecarbothioate 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%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + but-1-yn-4-yl thiobenzoate (211510-45-1) → 5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine (647852-33-3)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 22 - 24 ℃;

DOI:10.1081/NCN-120022030

Reference yield:

thiobenzoic acid (98-91-9) → 5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine (647852-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h / 0 - 20 °C

2: 96 percent / Et₃N; CuI / Pd(PPh₃)4 / dimethylformamide / 22 - 24 °C

With copper(l) iodide; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1081/NCN-120022030

Reference yield:

C26H46N2O8SSi2 → 5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine (647852-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / -55 - 20 °C

2: pyridine; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride / tetrahydrofuran / 16 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/c1cc14008f

upstream raw materials:

5-Iodo-2'-deoxyuridine

but-1-yn-4-yl thiobenzoate

thiobenzoic acid

2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine

Downstream raw materials:

1-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-(4-tert-butyldisulfanyl-but-1-ynyl)-1H-pyrimidine-2,4-dione

5-(4-benzoylthiobut-1-ynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine

Refernces

• 1、 Held, Heike A.,Roychowdhury, Abhijit,Benner, Steven A.. "C-5 Modified nucleosides: Direct insertion of alkynyl-thio functionality in pyrimidines". . p. 391 - 404. Retrieved 2007/10/03.