Deoxyuridine triphosphate

Base Information

• Chemical Name: Deoxyuridine triphosphate
• CAS No.: 1173-82-6
• Molecular Formula: C₉H₁₅N₂O₁₄P₃
• Molecular Weight: 468.144
• DSSTox Substance ID: DTXSID60908053
• Nikkaji Number: J315.490D
• Wikidata: Q28529690
• NCI Thesaurus Code: C104002
• Metabolomics Workbench ID: 37652
• ChEMBL ID: CHEMBL374361
• Mol file: 1173-82-6.mol

Synonyms:2'-deoxyuridine 5'-triphosphate;deoxy-UTP;deoxyuridine triphosphate

Chemical Property of Deoxyuridine triphosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 273.57000
• Density: 2.01g/cm³
• LogP: -1.47170
• XLogP3: -5.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 8
• Exact Mass: 467.97361415
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

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

((2R,3S,5R)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-3-HYDROXYTETRAHYDROFURAN-2-YL)METHYL TETRAHYDROGEN TRIPHOSPHATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1C(C(OC1N2C=CC(=O)NC2=O)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O

Technology Process of Deoxyuridine triphosphate

There total 8 articles about Deoxyuridine 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: 12.0%

C9H14N2O15P4 → 2'-deoxyuridine-5'-triphosphate (1173-82-6,94234-60-3)

Guidance literature:

With pyridine; water; iodine; In N,N-dimethyl-formamide; at 20 ℃; for 2.25h;

Reference yield:

C14H22N3O7P → 2'-deoxyuridine-5'-triphosphate (1173-82-6,94234-60-3)

Guidance literature:

With tris(tetra-n-butylammonium) hydrogen pyrophosphate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol049267j

Reference yield:

(4-Chloro-butyl)-methyl-phosphoramidic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester → 2'-deoxyuridine-5'-triphosphate (1173-82-6,94234-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / tetrahydrofuran / 2 h / 20 °C

2: 52 mg / tris(tetra-n-butylammonium) hydrogen pyrophosphate / tetrahydrofuran / 0.5 h / 20 °C

With hydrogen; tris(tetra-n-butylammonium) hydrogen pyrophosphate; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/ol049267j

upstream raw materials:

uridine

2'-deoxyuridine-5'-monophosphate

2'-deoxyuridine

Downstream raw materials:

dUDP

kanamycin A 3'-phosphate

8-iodo-2'-deoxyuridine-5'-O-triphosphate

dUDP-Glc

Refernces

• 1、 Kore, Anilkumar R.,Shanmugasundaram, Muthian,Senthilvelan, Annamalai,Srinivasan, Balasubramanian. "An improved protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′-triphosphates". experimental part. p. 423 - 431. Retrieved 2012/08/14.
• 2、 Ahmadibeni, Yousef,Parang, Keykavous. "Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides". . p. 5589 - 5592. Retrieved 2007/10/03.