(2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• CAS No.: 266360-65-0
• Molecular Formula: C10H12N6O6
• Molecular Weight: 312.242
• DSSTox Substance ID: DTXSID50446217
• Nikkaji Number: J1.257.213A
• Wikidata: Q82264814
• ChEMBL ID: CHEMBL2113493
• Mol file: 266360-65-0.mol

Synonyms:266360-65-0;CHEMBL2113493;(2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;2-nitroadenosine;SCHEMBL3749410;DTXSID50446217;BDBM50451108;(2R,3R,4S,5R)-2-(6-amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;(2R,3R,4S,5R)-2-(6-amino-2-nitropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property of (2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Chemical Property:

• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 2
• Exact Mass: 312.08183212
• Heavy Atom Count: 22
• Complexity: 437

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)[N+](=O)[O-])N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)[N+](=O)[O-])N

Technology Process of (2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

There total 2 articles about (2R,3R,4S,5R)-2-(6-Amino-2-nitro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 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: 10.0%

2-nitroadenosine pentaacetate (266360-70-7) → 2-Methoxyadenosine (24723-77-1) + 2-nitroadenosine (266360-65-0)

Guidance literature:

With potassium cyanide; In methanol;

DOI:10.1016/S0040-4039(99)02271-6

Reference yield:

methanol (67-56-1) + 6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine (266360-74-1) → 2-Methoxyadenosine (24723-77-1) + 2-nitroadenosine (266360-65-0)

Guidance literature:

With ammonium hydroxide; at 50 ℃; for 0.5h;

DOI:10.1081/NCN-120014815

Reference yield:

2-fluoro-6-N,N-dibenzoyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine + 2-nitropentabenzoyladenosine + 2-nitroadenosine (266360-65-0) → 2-fluoroadenosine (146-78-1)

Guidance literature:

With Bu₄NF; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

2-nitroadenosine pentaacetate

methanol

6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine

Downstream raw materials:

2-fluoroadenosine