132194-27-5

Basic information

• Product Name: [(2S,5R)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol
• Synonyms: 2,6-Dichloro-9-(2,3-dideoxy-.beta.-D-glycero-pentofuranosyl)-9H-purine; 2,6-Dichloro-9-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)-9H-purine
• CAS NO: 132194-27-5
• Molecular Formula: C₁₀H₁₀Cl₂N₄O₂
• Molecular Weight: 289.118
• Mol File: 132194-27-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 470.4°C at 760 mmHg
• Flash Point: 238.3°C
• Density: 1.86g/cm³
• Vapor Pressure: 1.18E-09mmHg at 25°C
• Refractive Index: 1.785
• CAS DataBase Reference: [(2S,5R)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,5R)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(132194-27-5)
• EPA Substance Registry System: [(2S,5R)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(132194-27-5)

Safety Data

• Hazardous Substances Data: 132194-27-5(Hazardous Substances Data)

Usage

General Description

The chemical compound [(2S,5R)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol is a complex organic molecule consisting of a tetrahydrofuran ring linked to a purine group and a methanol group. The compound has a specific stereochemistry, with the (2S,5R) configuration indicating the arrangement of the substituents around the tetrahydrofuran ring. The presence of dichloro-9H-purin-9-yl moiety suggests a purine nucleoside or nucleotide derivative, which could potentially make it a building block for pharmaceuticals or biological research. The methanol moiety also provides potential for chemical modification or reaction with other molecules. Overall, the compound represents an intriguing and potentially valuable molecule with diverse potential applications in the fields of medicine, biochemistry, and chemical synthesis.

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 5983-09-5 2',3'-Dideoxyuridine 

Relevant articles and documents

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.