149712-92-5

Basic information

• Product Name: N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
• Synonyms: N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
• CAS NO: 149712-92-5
• Molecular Weight: 305.384
• Mol File: 149712-92-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide(149712-92-5)
• EPA Substance Registry System: N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide(149712-92-5)

Safety Data

• Hazardous Substances Data: 149712-92-5(Hazardous Substances Data)

Upstream product

• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 10357-07-0 N-benzoyl-5-fluorocytosine 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 149819-37-4 (-)-(2S,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 149819-36-3 (+)-(2S,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 959348-89-1 N-[1-((2R,4R)-2-Benzyloxymethyl-2-methyl-[1,3]dioxolan-4-yl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 959324-93-7 N-[1-((2S,4R)-2-Benzyloxymethyl-2-methyl-[1,3]dioxolan-4-yl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 698391-74-1 5-fluoro-N⁴-benzoyl-1-(5-O-benzoyl-2,3-dideoxy-3,3-difluoro-β-D-ribofuranosyl)cytosine 

Relevant articles and documents

Stereoselective synthesis of rac-4′-ethynyl-2′-deoxy- and 4′-ethynyl-2′,3′-dideoxy-2′,3′- didehydronucleoside analogues

Synthesis of a racemic 4′-ethynyl-2′-deoxyribose intermediate using stereoselective chelation control is presented. This intermediate is further transformed to 4′-ethynyl-2′-deoxy- and 4′-ethynyl- 2′,3′-dideoxy-2′,3′-didehydronucleoside analogues. Georg T

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.