145986-21-6

Basic information

• Product Name: (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine
• Synonyms: (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine
• CAS NO: 145986-21-6
• Molecular Weight: 606.217
• Mol File: 145986-21-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine(145986-21-6)
• EPA Substance Registry System: (+)-(2R,5R)-5-chloro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine(145986-21-6)

Safety Data

• Hazardous Substances Data: 145986-21-6(Hazardous Substances Data)

Upstream product

• 1025959-81-2 tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane 
• 139689-04-6 (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid 
• 148774-90-7 (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde 
• 324015-67-0 (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane 
• 149712-93-6 N-(5-Chloro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide 
• 139757-71-4 (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane 

Downstream Products

• 137530-42-8 (+)-(2R,5R)-5-chloro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 

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.