120503-34-6

Basic information

• Product Name: (2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol
• Synonyms: (2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol;6-Chloro-9-(2,3-dideoxy-β-D-ribofuranosyl)-9H-purine;6-Chloropurine 2',3'-dideoxyriboside
• CAS NO: 120503-34-6
• Molecular Formula: C₁₀H₁₁ClN₄O₂
• Molecular Weight: 254.67
• Mol File: 120503-34-6.mol

Chemical Properties

• Melting Point: 97-99 °C
• Boiling Point: 486°C at 760 mmHg
• Flash Point: 247.7°C
• Appearance: /
• Density: 1.74g/cm³
• Vapor Pressure: 2.93E-10mmHg at 25°C
• Refractive Index: 1.773
• PKA: 14.44±0.10(Predicted)
• CAS DataBase Reference: (2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol(120503-34-6)
• EPA Substance Registry System: (2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol(120503-34-6)

Safety Data

• Hazardous Substances Data: 120503-34-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11ClN4O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2/t6-,7+/m0/s1

Upstream product

• 87-42-3 6-chloropurine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 69655-05-6 Dideoxyinosine 

Relevant articles and documents

A Highly Stereoselective Synthesis of Anti-HIV 2',3'-Dideoxy- and 2',3'-Didehydro-2',3'-dideoxynucleosides

A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

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.