145986-42-1

Basic information

• Product Name: [(2R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol
• Synonyms: 1,3-Oxathiolane-2-methanol, 5-(6-amino-2-fluoro-9H-purin-9-yl)-, (2R-trans)-
• CAS NO: 145986-42-1
• Molecular Formula: C₉H₁₀FN₅O₂S
• Molecular Weight: 271.2714
• Mol File: 145986-42-1.mol

Chemical Properties

• Boiling Point: 674.3°C at 760 mmHg
• Flash Point: 361.6°C
• Density: 2.01g/cm³
• Vapor Pressure: 4.21E-19mmHg at 25°C
• Refractive Index: 1.87
• CAS DataBase Reference: [(2R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(145986-42-1)
• EPA Substance Registry System: [(2R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(145986-42-1)

Safety Data

• Hazardous Substances Data: 145986-42-1(Hazardous Substances Data)

Upstream product

• 145913-78-6 (+)-(2R,5S)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 1651-29-2 6-chloro-2-fluoropurine 
• 149712-96-9 2-fluoro-6-chloropurine 
• 145986-40-9 (+)-(2R,5R)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 149819-68-1 (-)(2S,5S)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 149819-67-0 (-)(2S,5R)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 

Relevant articles and documents

Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents

In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.

Structure-Activity Relationships of β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanyl Nucleosides as Potential Anti-HIV Agents

The β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.The key intermediate 14, which was uti