126502-08-7

Basic information

• Product Name: [(2S,5R)-5-(9H-purin-9-yl)tetrahydrofuran-2-yl]methanol
• Synonyms: 2-furanmethanol, tetrahydro-5-(9H-purin-9-yl)-, (2S,5R)-; 9-(2,3-Dideoxy-.beta.-D-ribofuranosyl)-9H-purine; 9-(2,3-Dideoxy-beta-D-ribofuranosyl)-9H-purine
• CAS NO: 126502-08-7
• Molecular Formula: C₁₀H₁₂N₄O₂
• Molecular Weight: 220.2279
• Mol File: 126502-08-7.mol

Chemical Properties

• Boiling Point: 457.4°C at 760 mmHg
• Flash Point: 230.4°C
• Density: 1.61g/cm³
• Vapor Pressure: 3.7E-09mmHg at 25°C
• Refractive Index: 1.761
• CAS DataBase Reference: [(2S,5R)-5-(9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,5R)-5-(9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(126502-08-7)
• EPA Substance Registry System: [(2S,5R)-5-(9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(126502-08-7)

Safety Data

• Hazardous Substances Data: 126502-08-7(Hazardous Substances Data)

Upstream product

• 120-73-0 purine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 120-73-0 purine 

Downstream Products

• 120-73-0 purine 
• 122999-44-4 2,3-Didesoxy-β-D-glycero-pentofuranose 

Relevant articles and documents

Purine nucleoside synthesis from uridine using immobilised Enterobacter gergoviae CECT 875 whole cells

Biocatalysed purine nucleoside synthesis was carried out using immobilised Enterobacter gergoviae CECT 875. Similar yields (80-95%) in adenosine were obtained with both free and immobilised cells though in the last case a long reaction time was necessary. The immobilised cells can be reused at least for more than 30 times without significant loss of enzymatic activity. The immobilised biocatalyst in agarose is active in the synthesis of unnatural nucleosides.

Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2',3'-dideoxypurine nucleosides

A series of 6-substituted 2',3'-dideoxypurine ribofuranosides (ddP) was enzymatically synthesized with live E. coli in an effort to enhance the lipophilicity of this class of anti-human immunodeficiency virus (HIV) compounds and thereby facilitate drug delivery into the central nervous system. All 6-halo-substituted ddPs were substantially more lipophilic, as defined by their octanol-water partition coefficient (P), than their nonhalogenated congeners 2',3'-dideoxyinosine (ddI) or 2',3'-dideoxyguanosine (ddG). For this class of compounds, log P's ranged from +0.5 to -1.2 in the following order: 6-iodo, 2-amino-6-iodo > 6-bromo, 2-amino-6-bromo > 6-chloro, 2-amino-6-chloro > 6-fluoro, 2-amino-6-fluoro >> ddG > ddI. These compounds were evaluated in vitro for ability to suppress the infectivity, replication, and cytopathic effect of HIV. 2-Amino-6-fluoro-, 2-amino-6-chloro-, and 6-fluoro-ddP exhibited a potent activity against HIV comparable to that of ddI or ddG and completely blocked the infectivity of HIV without affecting the growth of target cells. The comparative order of in vitro anti-HIV activity was 2-amino-6-fluoro, 2-amino-6-chloro, 6-fluoro > 2-amino-6-bromo > 2-amino-6-iodo, 6-chloro > 6-bromo > 6-iodo. These compounds also exhibited potent in vitro activity against HIV-2 and 3'-azido-3'-deoxythymidine-resistant HIV-1 variants. All 2-amino-6-halo-ddPs and 6-halo-ddPs were substrates for adenosine deaminase (ADA) and were converted to ddG or ddI, respectively. In the presence of the potent ADA inhibitor 2'-deoxycoformycin, 6-halo-substituted ddPs failed to exert an in vitro antiretroviral effect. These dideoxypurine nucleoside analogues represent a new class of lipophilic prodrugs of ddG and ddI that possess the potential for more effective therapy of HIV-induced neurologic disorders.