9-beta-D-Xylofuranosyladenine

Base Information

• Chemical Name: 9-beta-D-Xylofuranosyladenine
• CAS No.: 524-69-6
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• DSSTox Substance ID: DTXSID30859028
• Nikkaji Number: J263.919J
• Wikidata: Q27120653
• Metabolomics Workbench ID: 148039
• ChEMBL ID: CHEMBL1236872
• Mol file: 524-69-6.mol

Synonyms:9 beta-D-xylofuranosyladenine;9 beta-D-xylosyladenine;9-xylosyladenine;9-xylosyladenine, ((9alpha)-(L))-isomer;xyloA;xylosyladenosine

Chemical Property of 9-beta-D-Xylofuranosyladenine

Chemical Property:

• Vapor Pressure: 3.26E-19mmHg at 25°C
• Melting Point: 125-140 °C
• Boiling Point: 676.3°Cat760mmHg
• PKA: 13.11±0.70(Predicted)
• Flash Point: 362.8°C
• PSA: 139.54000
• Density: 2.08g/cm³
• LogP: -1.39880
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@H]([C@H](O3)CO)O)O)N

Technology Process of 9-beta-D-Xylofuranosyladenine

There total 12 articles about 9-beta-D-Xylofuranosyladenine 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: 41.5%

9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) → (2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol (20535-16-4) + 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (20187-82-0,20227-41-2,64183-27-3,123334-75-8) + adenine xyloside (524-69-6)

Guidance literature:

With dibenzo-18-crown-6; potassium hydrogen bifluoride; In dimethyl sulfoxide; at 130 - 135 ℃; for 16h;

DOI:10.1002/recl.19951140202

Reference yield:

9-(3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine → adenosine (58-61-7) + adenine xyloside (524-69-6)

Guidance literature:

With tri-n-butyl-tin hydride; In methanol; at 20 ℃; for 2.5h; Title compound not separated from byproducts; Photolysis;

DOI:10.1021/ja962974q

Reference yield:

9-(3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine → adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + 2,3-dihydro-2-hydroxymethylfuran-3-one + adenosine (58-61-7) + adenine xyloside (524-69-6)

Guidance literature:

With tris[3-(2-methoxyethoxy)propyl]stannane; triethylammonium acetate; In water; acetonitrile; at 20 ℃; for 0.0833333h; pH=7; Photolysis;

DOI:10.1021/ja962974q

upstream raw materials:

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

2',3'-isopropylidene adenosine

adenosine 2',3'-cyclic monophosphate

2'-deoxy-D-adenosine

Downstream raw materials:

(1R)-1-(6-amino-purin-9-yl)-O⁵-trityl-D-1,4-anhydro-xylitol

9-(3,5-O-isopropylidene-β-D-xylofuranosyl)adenine

(6aR)-4-amino-8c-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-ol

endo-2',3'-O-decylideneadenosine