9-(beta-D-ribofuranosyl)uric acid

Base Information

• Chemical Name: 9-(beta-D-ribofuranosyl)uric acid
• CAS No.: 21082-30-4
• Molecular Formula: C10H12N4O7
• Molecular Weight: 300.228
• DSSTox Substance ID: DTXSID40175307
• Nikkaji Number: J2.328.067A
• Wikidata: Q27122110
• Metabolomics Workbench ID: 57452
• Mol file: 21082-30-4.mol

Synonyms:9-N-ribofuranosyluric acid;9-ribosyluric acid

Chemical Property of 9-(beta-D-ribofuranosyl)uric acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 173.43000
• Density: 1.96g/cm³
• LogP: -3.68230
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 300.07059873
• Heavy Atom Count: 21
• Complexity: 562

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(O1)N2C3=C(C(=O)NC(=O)N3)NC2=O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@H]([C@@H](O1)N2C3=C(C(=O)NC(=O)N3)NC2=O)O)O)O

Technology Process of 9-(beta-D-ribofuranosyl)uric acid

There total 15 articles about 9-(beta-D-ribofuranosyl)uric acid 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: 72.0%

2',3'-di-O-acetyl-2,6,8-tris<(p-nitrophenyl)ethoxy>-9-(β-D-ribofuranosyl)-9H-purine (102562-17-4) → 9-β-(D-ribofuranosyl)-1H-purine-2,6,8(3H,7H,9H)-trione (21082-30-4,5265-55-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 100 ℃; for 1.5h;

DOI:10.1002/hlca.19870700126

Reference yield: 70.0%

8-benzyloxy-xanthosine (3868-37-9) → 9-β-(D-ribofuranosyl)-1H-purine-2,6,8(3H,7H,9H)-trione (21082-30-4,5265-55-4)

Guidance literature:

With palladium on carbon; hydrogen;

DOI:10.1016/j.tetlet.2010.11.123

Reference yield: 61.0%

8-(benzyloxy)xanthosine (3868-37-9) → 9-(β-D-ribofuranosyl)uric acid (21082-30-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1021/jm00148a018

upstream raw materials:

2',3',5'-tri-O-acetyl-9-β-D-ribofuranosyl uric acid

2',3'-di-O-acetyl-2,6,8-tris<(p-nitrophenyl)ethoxy>-9-(β-D-ribofuranosyl)-9H-purine

2',3',5'-tri-O-acetyl-8-bromo-O⁶-<2(-p-nitrophenyl)ethyl>guanosine

2',3',5'-tri-O-acetyl-8-bromo-O⁶-<2-(p-nitrophenyl)ethyl>xanthosine

Downstream raw materials:

G

Refernces

• 1、 Schulz, Bernd S.,Pfleiderer, Wolfgang. "Nucleotides; Part XXXVI A New Synthesis of 9-(β-D-Ribofuranosyl)uric Acid and its 5'-Monophosphate". . p. 210 - 218. Retrieved 2007/10/02.
• 2、 Lin, Tai-Shun,Cheng, Jia-Chong,Ishiguro, Kimiko,Sartorelli, Alan C.. "Purine and 8-Substituted Purine Arabinofuranosyl and Ribofuranosyl Nucleoside Derivatives as Potential Inducers of the Differentiation of the Friend Erythroleuukemia". . p. 1481 - 1485. Retrieved 2007/10/02.