9-beta-D-Ribofuranosylxanthine

Base Information

• Chemical Name: 9-beta-D-Ribofuranosylxanthine
• CAS No.: 146-80-5
• Molecular Formula: C10H12N4O6
• Molecular Weight: 284.228
• Hs Code.: 29349990
• NSC Number: 18930
• Wikidata: Q105269557
• ChEMBL ID: CHEMBL1880013
• Mol file: 146-80-5.mol

Synonyms:9-.beta.-D-Ribofuranosylxanthine;.beta.-D-Ribofuranoside, xanthine-9;9-pentofuranosyl-3,9-dihydro-1H-purine-2,6-dione;NSC-18930;1H-Purine-2,6-dione, 3,9-dihydro-9-.beta.-D-ribofuranosyl-;SCHEMBL6676995;CHEMBL1880013;SCHEMBL21602879;9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione;UBORTCNDUKBEOP-UHFFFAOYSA-N;NSC18930;STK246877;STK681920;9-pentofuranosyl-9H-purine-2,6-diol;AKOS005422623;AKOS005596524;NCGC00161976-01;FT-0675871;FT-0770566;L000880;SR-01000091574;SR-01000091574-1;1H-Purine-2, 3,9-dihydro-9-.beta.-D-ribofuranosyl-;Z2651719377;9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-6-hydroxy-3H-purin-2(9H)-one?NSC 18930

Chemical Property of 9-beta-D-Ribofuranosylxanthine

Chemical Property:

• Vapor Pressure: 4.6E-29mmHg at 25°C
• Melting Point: 174～176℃
• Refractive Index: -52 ° (C=8, 0.3mol/L NaOH)
• Boiling Point: 828.2 °C at 760 mmHg
• PKA: pK1:<2.5(+1);pK2:5.67(0);pK3:12.00(-1) (25°C)
• Flash Point: 454.7 °C
• PSA: 153.46000
• Density: 2.25 g/cm³
• LogP: -2.97560
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 284.07568412
• Heavy Atom Count: 20
• Complexity: 434

Purity/Quality:

98% ^*data from raw suppliers

Xanthosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)NC(=O)NC2=O
• Uses: The deamination product of Guanosine. Potential biomarker for detecting radiation exposure. XANTHOSINE is used in the amplification of DNA isothermal strand displacement. Xanthosine-13C5, is the labeled analogue of Xanthosine (X742100), the deamination product of Guanosine. It is also a potential biomarker for detecting radiation exposure.

Technology Process of 9-beta-D-Ribofuranosylxanthine

There total 28 articles about 9-beta-D-Ribofuranosylxanthine 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: 97.0%

N1,N3-di(tert-butoxycarbonyl)-9-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)xanthine → xanthosine (146-80-5)

Guidance literature:

With water; trifluoroacetic acid; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00712-2

Reference yield: 81.0%

G (118-00-3) → xanthosine (146-80-5)

Guidance literature:

With oxygen; nitrogen(II) oxide; In dimethyl sulfoxide; for 1h; Ambient temperature;

DOI:10.1016/00404-0399(50)1715T-

Reference yield: 13.0%

N1-hydroxyinosine (5383-06-2) → 5-amino-3-β-D-ribofuranosyl-3H-imidaso<4,5-d><1,3>oxazin-7-one (80394-72-5) + Inosine (58-63-9) + xanthosine (146-80-5)

Guidance literature:

In water; for 2h; Ambient temperature; Irradiation;

DOI:10.1016/S0040-4039(98)01605-0

upstream raw materials:

G

N¹-hydroxyinosine

5-amino-1-(5′-O-tert-butyldimethylsilyl-2′,3′-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide

2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine

Downstream raw materials:

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

7-<(4-amino-1,2-dimethyl-5-pyrimidinio)methyl>xanthine perchlorate

9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-xanthosine

2-O-(R)-Formyl-(xanthin-9-yl)methyl-(R)-glyceraldehyde

Refernces

• 1、 Kojima, Naoshi,Minakawa, Noriaki,Matsuda, Akira. "Nucleosides and nucleotides. Part 207: Studies in the chemical conversion of the 4-carboxamide group of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside). Application for the synthesis of 1-deazaguanosine". . p. 7909 - 7914. Retrieved 2000.
• 2、 Oka, Natsuhisa,Hirabayashi, Hiroki,Kumada, Kota,Ando, Kaori. "Synthesis of xanthosine 2-phosphate diesters via phosphitylation of the carbonyl group". . . Retrieved 2021/11/16.
• 3、 Meier, Lidiane,Monteiro, Gustavo C.,Baldissera, Rodrigo A.M.,Sa?, Marcus Mandolesi. "Simple method for fast deprotection of nucleosides by triethylamine- catalyzed methanolysis of acetates in aqueous medium". experimental part. p. 859 - 866. Retrieved 2010/09/11.