Uridine5'-(tetrahydrogen triphosphate), 3'-deoxy- (9CI)

Base Information

• Chemical Name: Uridine5'-(tetrahydrogen triphosphate), 3'-deoxy- (9CI)
• CAS No.: 69199-40-2
• Molecular Formula: C₉H₁₅N₂O₁₄P₃
• Molecular Weight: 468.144
• Mol file: 69199-40-2.mol

Synonyms:3'-DeoxyUTP; 3'-Deoxyuridine-5'-triphosphate

Chemical Property of Uridine5'-(tetrahydrogen triphosphate), 3'-deoxy- (9CI)

Chemical Property:

• PSA: 273.83000
• Density: 2.01g/cm3
• LogP: -1.05940

Purity/Quality:

97% ^*data from raw suppliers

3'-Deoxyuridine-5'-triphosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Uridine5'-(tetrahydrogen triphosphate), 3'-deoxy- (9CI)

There total 13 articles about Uridine5'-(tetrahydrogen triphosphate), 3'-deoxy- (9CI) 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:

5-(6-amino-1-hexynyl)-3'-deoxyuridine-5'-triphosphate + FAM-(Pro)8-Lys(εTMR) + di(succinimido) carbonate (74124-79-1) → 3'-dUTP (69199-40-2)

Guidance literature:

With dmap; In water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

1-O-acetyl-2,5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose → 3'-dUTP (69199-40-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / TMS-triflate / acetonitrile / 24 h / Ambient temperature

2: 91.2 percent / hydrazine hydrate / acetic acid; pyridine / Ambient temperature

3: 96 percent / sodium nitrite, fluoroacetic acid / 5 h / 0 °C

4: 65.8 percent / 0.05 N methanolic sodium methoxide / 3 h / 50 °C

5: 78 percent / phosphoryl chloride, triethylphosphate / 12 h / 0 °C

6: 1.) N,N'carbonyldiimidazole, 2.) tri-n-butylammonium pyrophosphate / 1.) DMF, RT, 3.5 h, 2.) DMF, RT, 24 h

With triethyl phosphate; Fluoroacetic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; tri(n-butyl)ammonium pyrophosphate; hydrazine hydrate; 1,1'-carbonyldiimidazole; sodium nitrite; trichlorophosphate; In pyridine; acetic acid; acetonitrile;

DOI:10.1248/cpb.43.2005

Reference yield:

2',5'-di-O-p-chlorobenzoyl-N4-propionyl-3'-deoxycytidine (173601-08-6) → 3'-dUTP (69199-40-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 91.2 percent / hydrazine hydrate / acetic acid; pyridine / Ambient temperature

2: 96 percent / sodium nitrite, fluoroacetic acid / 5 h / 0 °C

3: 65.8 percent / 0.05 N methanolic sodium methoxide / 3 h / 50 °C

4: 78 percent / phosphoryl chloride, triethylphosphate / 12 h / 0 °C

5: 1.) N,N'carbonyldiimidazole, 2.) tri-n-butylammonium pyrophosphate / 1.) DMF, RT, 3.5 h, 2.) DMF, RT, 24 h

With triethyl phosphate; Fluoroacetic acid; sodium methylate; tri(n-butyl)ammonium pyrophosphate; hydrazine hydrate; 1,1'-carbonyldiimidazole; sodium nitrite; trichlorophosphate; In pyridine; acetic acid;

DOI:10.1248/cpb.43.2005

upstream raw materials:

((2R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxytetrahydrofuran-2-yl)methyl phosphate

3'-deoxyuridine

2',5'-di-O-p-chlorobenzoyl-3'-deoxycytidine

2',5'-di-O-p-chlorobenzoyl-3'-deoxyuridine

Refernces

• 1、 -. "Compounds having energy transfer function and method for DNA base sequencing by using the same". . . Retrieved 2008/06/13.
• 2、 Saneyoshi,Kohsaka-Ichikawa,Yahata,Kimura,Izuta,Yamaguchi. "Synthetic nucleosides and nucleotides. XXXV. Synthesis and biological evaluations of 5-fluoropyrimidine nucleosides and nucleotides of 3-deoxy-β- D-ribofuranose and related compounds". . p. 2005 - 2009. Retrieved 2007/10/03.