Uracil arabinose-5'-phosphate

Base Information

• Chemical Name: Uracil arabinose-5'-phosphate
• CAS No.: 18354-06-8
• Molecular Formula: C9H13 N2 O9 P
• Molecular Weight: 324.184
• UNII: IYD0EF6ZRI
• Nikkaji Number: J2.150.743A
• Wikidata: Q27466836
• Mol file: 18354-06-8.mol

Synonyms:18354-06-8;Uracil arabinotide;URACIL ARABINOSE-5'-PHOSPHATE;1-beta-D-Arabinofuranosyluracil 5'-Monophosphate;IYD0EF6ZRI;[(2R,3S,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;Uracil Arabinonucleoside 5'-Phosphate;UNII-IYD0EF6ZRI;SCHEMBL2056713;CHEBI:190946;LS-194361;1-?-D-Arabinofuranosyluracil 5'-Monophosphate;1-(5-O-Phosphono-beta-D-arabinofuranosyl)uracil;1- beta -D-Arabinofuranosyluracil 5'-Monophosphate;J-011754;Q27466836;1-.BETA.-D-ARABINOFURANOSYLURACIL 5'-MONOPHOSPHATE;Uracil, 1-beta-D-arabinofuranosyl-, 5'-(dihydrogen phosphate);1-(5-O-Phosphono-beta-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione;1-(5-O-phosphono-beta-D-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione;URACIL, 1-.BETA.-D-ARABINOFURANOSYL-, 5'-(DIHYDROGEN PHOSPHATE);2,4(1H,3H)-PYRIMIDINEDIONE, 1-(5-O-PHOSPHONO-.BETA.-D-ARABINOFURANOSYL)-;((2R,3S,4S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

Chemical Property of Uracil arabinose-5'-phosphate

Chemical Property:

• PSA: 181.12000
• Density: 1.865g/cm3
• LogP: -2.73490
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Water
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 324.03586699
• Heavy Atom Count: 21
• Complexity: 517

Purity/Quality:

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

1-β-D-Arabinofuranosyluracil5''-Monophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
• Uses: A metabolite of 1-β-D-Arabinofuranosyluracil. A metablite of 1-?D-Arabinofuranosyluracil A metablite of 1-β-D-Arabinofuranosyluracil.

Technology Process of Uracil arabinose-5'-phosphate

There total 15 articles about Uracil arabinose-5'-phosphate 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: 45.0%

araU (3083-77-0) → arabinosyluracil-5'-monophosphate (18354-06-8,27416-86-0)

Guidance literature:

With triethyl phosphate; trichlorophosphate;

DOI:10.1002/mrc.1260231102

Reference yield: 37.0%

L-uridine (58-96-8) → L-uridine 5'-monophosphate (58-97-9,14522-18-0,18354-06-8,22256-97-9,22256-98-0,25314-57-2,29740-87-2,73206-51-6,96789-08-1,27416-86-0)

Guidance literature:

With triethyl phosphate; trichlorophosphate; at 0 ℃; for 22h;

DOI:10.1016/j.tetlet.2003.09.142

Reference yield:

cytosine arabinoside-5'-monophosphate (7075-11-8,30811-80-4) → arabinosyl cytosine (147-94-4) + arabinosyluracil-5'-monophosphate (18354-06-8,27416-86-0)

Guidance literature:

With ethylenediaminetetraacetic acid; glycine; sodium chloride; at 90 ℃; pH=7.5; Kinetics;

DOI:10.1021/jo800317e

upstream raw materials:

L-uridine

(2S,3S,4S,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

araU

2,2'-Anhydrouridine

Refernces

• 1、 Joshi, Prakash C.,Aldersley, Michael F.,Zagorevskii, Dmitri V.,Ferris, James P.. "A nucleotide dimer synthesis without protecting groups using montmorillonite as catalyst". experimental part. p. 536 - 566. Retrieved 2012/10/08.
• 2、 Miyashita, Takanori,Sakata, Shinji,Hayakawa, Hiroyuki. "First synthesis of enantio-uracil dinucleotide, comparison of physicochemical properties of their enantiomers, and separation by chiral column chromatography". . p. 8605 - 8607. Retrieved 2007/10/03.