238096-55-4

Basic information

• Product Name: N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide
• Synonyms: N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide
• CAS NO: 238096-55-4
• Molecular Weight: 287.393
• Mol File: 238096-55-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide(238096-55-4)
• EPA Substance Registry System: N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide(238096-55-4)

Safety Data

• Hazardous Substances Data: 238096-55-4(Hazardous Substances Data)

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 26661-13-2 4-N-benzoylcytosine 
• 107-46-0 Hexamethyldisiloxane 
• 4039-32-1 lithium hexamethyldisilazane 
• 98-88-4 benzoyl chloride 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 287737-67-1 3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-4-N-benzoylcytidine 
• 1496551-70-2 2'-deoxy-2'-chloro-2'-C-methyl-3',5'-di-O-benzoyl-N⁴-benzoylcytidine 
• 874638-98-9 N-(1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 1418141-27-1 C₂₃H₃₂FN₃O₅Si 
• 1583260-54-1 N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 1583260-53-0 N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 927420-27-7 C₄₆H₄₅N₃O₇ 
• 927420-80-2 C₄₆H₄₅N₃O₇ 
• 210548-37-1 N-[1-((2R,4R,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 273204-58-3 (2S,3R,4R,5R)-2-[2-(Benzoylamino)-2-oxo-1,2-dihydropyrimidin-1-yl]-5-({2-[(2,3-dihydroxy-5-nitrobenzoyl)amino]ethoxy}methyl)tetrahydrofuran-3,4-diyl diacetate 
• 476210-04-5 N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]cytosine 
• 864858-41-3 [(1S,3R,4R,5S)-4-(acetyloxy)-3-(4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl)-2-oxabicyclo[3.1.0]hex-1-yl]methyl acetate 
• 476209-96-8 (+)-N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine 
• 405238-85-9 1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine 

Relevant articles and documents

Synthesis and Anti-HCV Activities of 4′-Fluoro-2′-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4′-Fluoro-2′- C-methyluridine 5′-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection

We report the synthesis and biological evaluation of a series of 4′-fluoro-2′-C-substituted uridines. Triphosphates of the uridine analogues exhibited a potent inhibition of hepatitis C virus (HCV) NS5B polymerase with IC50 values as low as 27 nM. In an HCV subgenomic replicon assay, the phosphoramidate prodrugs of these uridine analogues demonstrated a very potent activity with EC50 values as low as 20 nM. A lead compound AL-335 (53) demonstrated high levels of the nucleoside triphosphate in vitro in primary human hepatocytes and Huh-7 cells as well as in dog liver following a single oral dose. Compound 53 was selected for the clinical development where it showed promising results in phase 1 and 2 trials.

Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

New isoelectronic, non-isosteric phosphonate analogues of nucleoside 5'-phosphates featuring the phosphorus moiety directly attached on the sugar ring in the C4' position are described. The analogues were synthesised by a nucleosidation reaction from tetr

Ex-chiral-pool synthesis of β-hydroxyphosphonate nucleoside analogues

A new series of mononucleotide analogues bearing a nonhydrolysable P-C bond instead of the P-O phosphate linkage is presented. We intend to set up an approach that allows the synthesis of β-hydroxyphosphonate nucleoside analogues as a single diastereoisomer. In this respect, the key "sugar-phosphonate" intermediate was obtained through an Arbusov reaction from an iodosugar derivative in which the stereochemistry of the β-hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.