145986-37-4

Basic information

• Product Name: {(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-yl}methanol
• CAS NO: 145986-37-4
• Molecular Formula: C₁₀H₁₃N₅O₂S
• Molecular Weight: 267.3075
• Mol File: 145986-37-4.mol

Chemical Properties

• Boiling Point: 582.8°C at 760 mmHg
• Flash Point: 306.2°C
• Density: 1.72g/cm³
• Vapor Pressure: 2.01E-14mmHg at 25°C
• Refractive Index: 1.811
• CAS DataBase Reference: {(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-yl}methanol(CAS DataBase Reference)
• NIST Chemistry Reference: {(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-yl}methanol(145986-37-4)
• EPA Substance Registry System: {(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-yl}methanol(145986-37-4)

Safety Data

• Hazardous Substances Data: 145986-37-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-ylmethanol is used as a key compound in pharmaceutical research for its potential to interact with biological systems. Its unique structure allows it to be a promising candidate for the development of new drugs and therapies.
Used in Biochemical Research:
In the field of biochemical research, (2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-ylmethanol is utilized as a valuable compound for studying the interactions between various biological molecules. Its presence in DNA, RNA, and ATP, as well as its oxathiolane ring and methanol group, make it an interesting subject for understanding the mechanisms of cellular processes and potential therapeutic targets.
Used in Drug Development:
(2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-ylmethanol is employed as a starting material or intermediate in the synthesis of new drugs. Its unique structure and potential interactions with biological systems make it a valuable component in the development of novel therapeutic agents.
Used in Drug Delivery Systems:
Similar to gallotannin, (2R,5S)-2-[6-(methylamino)-9H-purin-9-yl]-1,3-oxathiolan-5-ylmethanol may also be used in the development of drug delivery systems. Its unique structure could be exploited to improve the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical compounds.

Upstream product

• 87-42-3 6-chloropurine 
• 32865-86-4 6-chloro-9-trimethylsilylpurine 
• 149819-57-8 (-)(2S,5R)-6-chloro-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>purine 
• 74-89-5 methylamine 
• 149819-58-9 (-)-(2S,5S)-6-chloro-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>purine 
• 145986-33-0 (+)-(2R,5R)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 145986-34-1 (+)-(2R,5R)-6-chloro-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>purine 
• 145913-73-1 (+)-(2R,5S)-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 145913-74-2 (+)-(2R,5S)-6-chloro-9-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>purine 

Relevant articles and documents

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

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.