4-Thiouridine-5'-monophosphate

Base Information

• Chemical Name: 4-Thiouridine-5'-monophosphate
• CAS No.: 4145-46-4
• Molecular Formula: C9H13 N2 O8 P S
• Molecular Weight: 384.21
• ChEMBL ID: CHEMBL1230331
• Nikkaji Number: J756.680H
• Wikidata: Q27454935
• Mol file: 4145-46-4.mol

Synonyms:4-thiouracil 5'-monophosphate;4-thiouridylate;4-thiouridylic acid;4-thio-UMP;4-thiouridine monophosphate

Chemical Property of 4-Thiouridine-5'-monophosphate

Chemical Property:

• PKA: 1.86±0.10(Predicted)
• PSA: 205.61000
• Density: 1.88±0.1 g/cm3(Predicted)
• LogP: -0.86310
• Storage Temp.: −20°C
• XLogP3: -3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 340.01302355
• Heavy Atom Count: 21
• Complexity: 522

Purity/Quality:

97% ^*data from raw suppliers

4-THIOURIDINE-5'-MONOPHOSPHATE DISODIUM SALT 98.00% ^*data from reagent suppliers

Safty Information:

• Statements: 66
• Safety Statements: 24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=S)C2C(C(C(O2)COP(=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)O)O)O

Technology Process of 4-Thiouridine-5'-monophosphate

There total 7 articles about 4-Thiouridine-5'-monophosphate 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:

C9H11Cl2N2O6PS → 4-Thiouridin-5'-phosphat (4145-46-4)

Guidance literature:

With triethylamine carbonate; at 20 ℃;

DOI:10.1021/jm901432g

Reference yield:

4-thiouridine (13957-31-8) → 4-Thiouridin-5'-phosphat (4145-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate / triethyl phosphate / 5 h / Inert atmosphere; Cooling

2: water; triethylamine carbonate / 1 h / 20 °C / pH 7.4 - 7.6

With water; triethylamine carbonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate; In triethyl phosphate;

DOI:10.1021/jm1016297

Reference yield:

uridine (58-96-8) → 4-Thiouridin-5'-phosphat (4145-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 3 h / 60 °C

2: Lawessons reagent / benzene / 24 h / Reflux

3: ammonia / methanol / 12 h

4: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate / triethyl phosphate / 5 h / Inert atmosphere; Cooling

5: water; triethylamine carbonate / 1 h / 20 °C / pH 7.4 - 7.6

With Lawessons reagent; pyridine; ammonia; water; triethylamine carbonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate; In methanol; triethyl phosphate; benzene;

DOI:10.1021/jm1016297

upstream raw materials:

4-thiouridine

uridine

4-thio-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-(3H)-pyrimidine-2,4-dione

Tri-O-acetyluridine

Refernces

• 1、 Das, Arijit,Ko, Hyojin,Burianek, Lauren E.,Barrett, Matthew O.,Harden, T. Kendall,Jacobson, Kenneth A.. "Human P2Y14 receptor agonists: Truncation of the hexose moiety of uridine-5′-diphosphoglucose and its replacement with alkyl and aryl groups". scheme or table. p. 471 - 480. Retrieved 2010/05/02.
• 2、 Saneyoshi. "Direct thiation of uridine 5'-phosphate.". . p. 1400 - 1402. Retrieved 2007/11/30.