4-Thiouridine triphosphate

Base Information

• Chemical Name: 4-Thiouridine triphosphate
• CAS No.: 31556-28-2
• Molecular Formula: C₉H₁₅N₂O₁₄P₃S
• Molecular Weight: 500.21
• DSSTox Substance ID: DTXSID10953533
• Nikkaji Number: J2.386.071F
• Wikidata: Q27073960
• Pharos Ligand ID: LF4LHHH9GB2M
• ChEMBL ID: CHEMBL1767409
• Mol file: 31556-28-2.mol

Synonyms:4-S-UTP;4-thio-UTP;4-thiouridine triphosphate

Chemical Property of 4-Thiouridine triphosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 312.63000
• Density: 2.09g/cm³
• LogP: -1.50550
• XLogP3: -5.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 499.94568532
• Heavy Atom Count: 29
• Complexity: 844

Purity/Quality:

99%, ^*data from raw suppliers

4-Thiouridine-5'-triphosphate sodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=S)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=S)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O

Technology Process of 4-Thiouridine triphosphate

There total 6 articles about 4-Thiouridine triphosphate 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:

[(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate (82913-19-7) → 4-thiouridine 5'-triphosphate (31556-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂S / ethanol / Ambient temperature

2: aq. NH₃

With hydrogen sulfide; In ammonium hydroxide; ethanol;

DOI:10.1080/07328319708006141

Reference yield:

uridine (58-96-8) → 4-thiouridine 5'-triphosphate (31556-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / pyridine / 3 h / 60 °C

2: 65 percent / 4-chlorophenyldichlorophosphate / pyridine / 18 h / Ambient temperature

3: H₂S / ethanol / Ambient temperature

4: aq. NH₃

With hydrogen sulfide; 4-chlorophenylphosphorodichloridate; In pyridine; ammonium hydroxide; ethanol;

DOI:10.1080/07328319708006141

Reference yield:

Tri-O-acetyluridine (4105-38-8) → 4-thiouridine 5'-triphosphate (31556-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / 4-chlorophenyldichlorophosphate / pyridine / 18 h / Ambient temperature

2: H₂S / ethanol / Ambient temperature

3: aq. NH₃

With hydrogen sulfide; 4-chlorophenylphosphorodichloridate; In pyridine; ammonium hydroxide; ethanol;

DOI:10.1080/07328319708006141

upstream raw materials:

4-thio-uridine

[(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate

uridine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-mercapto-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Refernces

• 1、 Shaver, Sammy R.,Pendergast, William,Siddiqi, Suhaib M.,Yerxa, Benjamin R.,Croom, Dallas K.,Dougherty, Robert W.,James, Michael K.,Neil Jones,Rideout, Janet L.. "4-Substituted uridine 5′-triphosphates as agonists of the P2y2 purinergic receptor". . p. 1099 - 1102. Retrieved 2007/10/03.