[(2R,4R)-4-(6-aminopurin-9-yl)oxolan-2-yl]methanol

Base Information

• Chemical Name: [(2R,4R)-4-(6-aminopurin-9-yl)oxolan-2-yl]methanol
• CAS No.: 127682-75-1
• Molecular Formula: C10H13 N5 O2
• Molecular Weight: 235.2425
• DSSTox Substance ID: DTXSID40155624
• Nikkaji Number: J473.885C
• Wikidata: Q83023571
• ChEMBL ID: CHEMBL421506
• Mol file: 127682-75-1.mol

Synonyms:IsoddA;Ro 24-5098;Ro-24-5098;Ro24-5098

Chemical Property of [(2R,4R)-4-(6-aminopurin-9-yl)oxolan-2-yl]methanol

Chemical Property:

• Vapor Pressure: 2.14E-08mmHg at 25°C
• Boiling Point: 409°C at 760 mmHg
• Flash Point: 201.2°C
• Density: 1.76g/cm³
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 235.10692467
• Heavy Atom Count: 17
• Complexity: 279

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(COC1CO)N2C=NC3=C(N=CN=C32)N
• Isomeric SMILES: C1[C@H](CO[C@H]1CO)N2C=NC3=C(N=CN=C32)N

Technology Process of [(2R,4R)-4-(6-aminopurin-9-yl)oxolan-2-yl]methanol

There total 38 articles about [(2R,4R)-4-(6-aminopurin-9-yl)oxolan-2-yl]methanol 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: 100.0%

6-amino-9-[(3R,5R)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydrofuran-3-yl]purine (204509-06-8) → IsoddA (127682-75-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo9721655

Reference yield: 73.0%

(3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine (142941-43-3) → IsoddA (127682-75-1)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In methanol;

Reference yield: 35.0%

(2R-trans)-tetrahydro-4-[[(4-methylphenyl)-sulfonyl]oxy]-2-furanmethanol (127682-78-4) + 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) → IsoddA (127682-75-1)

Guidance literature:

With potassium carbonate; 18-crown-6 ether; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/S0040-4039(01)93867-5

upstream raw materials:

(2R-cis)-4-(6-chloro-9H-purin-9-yl)-tetrahydro-2-furanmethanol

4(R)-(6-amino-9H-purin-9-yl)-2(R)-tetrahydrofuranal

(3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine

(2R-trans)-tetrahydro-4-[[(4-methylphenyl)-sulfonyl]oxy]-2-furanmethanol

Refernces

• 1、 Franchetti, Palmarisa,Cappellacci, Loredana,Grifantini, Mario,Messini, Lea,Sheikha, Ghassan Abu,et al.. "Synthesis and Evaluation of the Anti-HIV Activity of Aza and Deaza Analogues of IsoddA and Their Phosphates as Prodrugs". . p. 3534 - 3541. Retrieved 1994.
• 2、 Jones, Martin F.,Noble, Stewart A.,Robertson, Colin A.,Storer, Richard,Highcock, Rona M.,Lamont, R. Brian. "Enantiospecific Synthesis of 3'-Hetero-dideoxy Nucleoside Analogues as Potential Anti-HIV Agents". . p. 1427 - 1436. Retrieved 2007/10/02.